diff --git a/.github/ISSUE_TEMPLATE/bug.yml b/.github/ISSUE_TEMPLATE/bug.yml
index f32660170..ffd2e5d7d 100644
--- a/.github/ISSUE_TEMPLATE/bug.yml
+++ b/.github/ISSUE_TEMPLATE/bug.yml
@@ -1,7 +1,9 @@
 name: Bug Report
 description: File a bug report
 title: "bug: <title>"
-labels: ["kind/Bug", "valuestream/SDK"]
+type: Fix
+assignees:
+  - edgarrmondragon
 
 body:
   - type: markdown
@@ -13,7 +15,7 @@ body:
     attributes:
       label: Singer SDK Version
       description: Version of the library you are using
-      placeholder: "0.41.0"
+      placeholder: "0.42.1"
     validations:
       required: true
   - type: checkboxes
@@ -29,13 +31,13 @@ body:
       label: Python Version
       description: Version of Python you are using
       options:
+        - "NA"
+        - "3.13"
         - "3.12"
         - "3.11"
         - "3.10"
         - "3.9"
-        - "3.8"
-        - "3.7 or earlier"
-        - "NA"
+        - "3.8 or earlier"
     validations:
       required: true
   - type: dropdown
@@ -60,7 +62,7 @@ body:
       description: What operating system you are using
       placeholder: "Windows"
     validations:
-      required: true
+      required: false
   - type: textarea
     id: what-happened
     attributes:
diff --git a/.github/ISSUE_TEMPLATE/docs.yml b/.github/ISSUE_TEMPLATE/docs.yml
index ca0d9c673..b47a9909d 100644
--- a/.github/ISSUE_TEMPLATE/docs.yml
+++ b/.github/ISSUE_TEMPLATE/docs.yml
@@ -1,7 +1,10 @@
 name: Documentation change
 description: Request a documentation change
 title: "docs: <title>"
+type: Docs
 labels: ["Documentation", "valuestream/SDK"]
+assignees:
+  - edgarrmondragon
 
 body:
   - type: markdown
diff --git a/.github/ISSUE_TEMPLATE/feature.yml b/.github/ISSUE_TEMPLATE/feature.yml
index a5afd5974..bf435a43d 100644
--- a/.github/ISSUE_TEMPLATE/feature.yml
+++ b/.github/ISSUE_TEMPLATE/feature.yml
@@ -2,8 +2,9 @@ name: Feature request
 description: Request a new feature
 title: "feat: <title>"
 labels: ["kind/Feature", "valuestream/SDK"]
+type: Feat
 assignees:
-  - meltano/engineering
+  - edgarrmondragon
 
 body:
   - type: markdown
@@ -16,7 +17,8 @@ body:
       label: Feature scope
       description: Functionality this new feature would impact
       options:
-        - Taps (catalog, state, stream maps, tests, etc.)
+        - Taps (catalog, state, tests, etc.)
+        - Inline mapping (stream maps, flattening, etc.)
         - Targets (data type handling, batching, SQL object generation, tests, etc.)
         - Configuration (settings parsing, validation, etc.)
         - CLI (options, error messages, logging, etc.)
diff --git a/.github/workflows/api-changes.yml b/.github/workflows/api-changes.yml
index c758517c4..108d5b6f0 100644
--- a/.github/workflows/api-changes.yml
+++ b/.github/workflows/api-changes.yml
@@ -30,7 +30,7 @@ jobs:
     - name: Setup Python
       uses: actions/setup-python@v5
       with:
-        python-version: 3.12
+        python-version: 3.x
 
     - name: Install tools
       env:
@@ -38,7 +38,6 @@ jobs:
       run: |
         python -Im pip install -U pip
         pipx install griffe nox
-        pipx inject nox nox-poetry
         pipx list
 
     - name: Set REF
diff --git a/.github/workflows/codeql-analysis.yml b/.github/workflows/codeql-analysis.yml
index 7f3194489..99f946341 100644
--- a/.github/workflows/codeql-analysis.yml
+++ b/.github/workflows/codeql-analysis.yml
@@ -8,7 +8,9 @@ name: "CodeQL"
 
 on:
   push:
-    branches: [ "main" ]
+    branches:
+      - "main"
+      - "v*"
     paths:
       - .github/workflows/codeql-analysis.yml
       - '**.py'  # Any Python file
diff --git a/.github/workflows/codspeed.yml b/.github/workflows/codspeed.yml
index 122e9d090..23d2f79eb 100644
--- a/.github/workflows/codspeed.yml
+++ b/.github/workflows/codspeed.yml
@@ -4,6 +4,7 @@ on:
   push:
     branches:
       - "main"
+      - "v*"
     paths:
       - "singer_sdk/**"
       - "tests/**"
@@ -30,7 +31,7 @@ jobs:
     - uses: actions/checkout@v4
     - uses: actions/setup-python@v5
       with:
-        python-version: 3.12
+        python-version: 3.x
         architecture: x64
 
     - name: Install poetry
diff --git a/.github/workflows/constraints.txt b/.github/workflows/constraints.txt
index 4dfd4edc8..9c097dc1a 100644
--- a/.github/workflows/constraints.txt
+++ b/.github/workflows/constraints.txt
@@ -1,8 +1,5 @@
-griffe==1.3.1
-pip==24.2
-poetry==1.8.3
-poetry-plugin-export==1.8.0
-poetry-dynamic-versioning==1.4.1
-pre-commit==3.8.0
-nox==2024.4.15
-nox-poetry==1.0.3
+griffe~=1.5
+pip==24.3.1
+poetry==1.8.4
+pre-commit==4.0.1
+nox==2024.10.9
diff --git a/.github/workflows/cookiecutter-e2e.yml b/.github/workflows/cookiecutter-e2e.yml
index 051d21d95..6bc9361fe 100644
--- a/.github/workflows/cookiecutter-e2e.yml
+++ b/.github/workflows/cookiecutter-e2e.yml
@@ -8,7 +8,9 @@ on:
     - "e2e-tests/cookiecutters/**"
     - ".github/workflows/cookiecutter-e2e.yml"
   push:
-    branches: [main]
+    branches:
+    - main
+    - v*
     paths:
     - "cookiecutter/**"
     - "e2e-tests/cookiecutters/**"
@@ -24,14 +26,8 @@ env:
 
 jobs:
   lint:
-    name: Cookiecutter E2E Python ${{ matrix.python-version }} / ${{ matrix.os }}
-    runs-on: ${{ matrix.os }}
-    strategy:
-      fail-fast: true
-      matrix:
-        include:
-          - { python-version: "3.12",  os: "ubuntu-latest" }
-
+    name: Cookiecutter E2E Python
+    runs-on: ubuntu-latest
     steps:
     - uses: actions/checkout@v4
     - name: Upgrade pip
@@ -46,38 +42,36 @@ jobs:
         PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
       run: |
         pipx install poetry
-        pipx inject poetry poetry-plugin-export
         poetry --version
-        poetry self show plugins
 
     - uses: actions/setup-python@v5
       with:
-        python-version: ${{ matrix.python-version }}
-        architecture: x64
-        cache: 'pip'
-        cache-dependency-path: 'poetry.lock'
+        python-version: 3.x
+
+    - uses: astral-sh/setup-uv@v3
+      with:
+        version: ">=0.4.30"
 
     - name: Install pre-commit
       run: |
-        pipx install pre-commit
+        uv tool install --with=pre-commit-uv pre-commit
         pre-commit --version
 
     - name: Install Nox
       env:
         PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
       run: |
-        pipx install nox
-        pipx inject nox nox-poetry
+        uv tool install nox
         nox --version
 
     - name: Run Nox
       run: |
-        nox --python=${{ matrix.python-version }} --session=test_cookiecutter
+        nox --session=test_cookiecutter
 
     - uses: actions/upload-artifact@v4
       if: always()
       with:
-        name: cookiecutter-${{ matrix.os }}-py${{ matrix.python-version }}
+        name: cookiecutter-ubuntu-latest-py3x
         path: |
           /tmp/tap-*
           /tmp/target-*
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 2c08df46e..1cd706cb6 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -65,7 +65,7 @@ jobs:
         name: Packages
         path: dist
     - name: Publish
-      uses: pypa/gh-action-pypi-publish@v1.10.2
+      uses: pypa/gh-action-pypi-publish@v1.12.2
 
   upload-to-release:
     name: Upload files to release
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 1613ebc5e..c911c9cf1 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -14,7 +14,9 @@ on:
       - ".github/workflows/test.yml"
       - ".github/workflows/constraints.txt"
   push:
-    branches: [main]
+    branches:
+      - main
+      - v*
     paths:
       - "cookiecutter/**"
       - "samples/**"
@@ -37,7 +39,7 @@ env:
 
 jobs:
   tests:
-    name: "Test on ${{ matrix.python-version }} (${{ matrix.session }}) / ${{ matrix.os }} / SQLAlchemy: ${{ matrix.sqlalchemy }}"
+    name: "Test on ${{ matrix.python-version }} (${{ matrix.session }}) / ${{ matrix.os }}"
     runs-on: ${{ matrix.os }}
     continue-on-error: true
     env:
@@ -48,32 +50,26 @@ jobs:
       matrix:
         session: [tests]
         os: ["ubuntu-latest", "macos-latest", "windows-latest"]
-        python-version: ["3.8", "3.9", "3.10", "3.11", "3.12"]
-        sqlalchemy: ["2"]
+        python-version:
+        - "3.9"
+        - "3.10"
+        - "3.11"
+        - "3.12"
+        - "3.13"
         include:
-        - { session: tests,   python-version: "3.12", os: "ubuntu-latest", sqlalchemy: "1" }
-        - { session: doctest, python-version: "3.12", os: "ubuntu-latest", sqlalchemy: "2" }
-        - { session: mypy,    python-version: "3.12",  os: "ubuntu-latest", sqlalchemy: "2" }
-        - { session: deps,    python-version: "3.12",  os: "ubuntu-latest", sqlalchemy: "2" }
+        - { session: doctest, python-version: "3.13", os: "ubuntu-latest" }
+        - { session: mypy,    python-version: "3.13", os: "ubuntu-latest" }
+        - { session: deps,    python-version: "3.13", os: "ubuntu-latest" }
 
     steps:
     - uses: actions/checkout@v4
       with:
         fetch-depth: 0
 
-    - name: Install Poetry
-      env:
-        PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
-      run: |
-        pipx install poetry
-        pipx inject poetry poetry-plugin-export
-        pipx inject poetry poetry-dynamic-versioning[plugin]
-        poetry --version
-        poetry self show plugins
-
     - uses: actions/setup-python@v5
       with:
         python-version: ${{ matrix.python-version }}
+        allow-prereleases: true
 
     - name: Upgrade pip
       env:
@@ -87,7 +83,6 @@ jobs:
         PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
       run: |
         pipx install 'nox[uv]'
-        pipx inject nox nox-poetry
         nox --version
 
     - uses: actions/cache@v4
@@ -98,7 +93,8 @@ jobs:
 
     - name: Run Nox
       env:
-        SQLALCHEMY_VERSION: ${{ matrix.sqlalchemy }}
+        PIP_PRE: "1"
+        UV_PRERELEASE: allow
       run: |
         nox --verbose
 
@@ -126,16 +122,6 @@ jobs:
       with:
         fetch-depth: 0
 
-    - name: Install Poetry
-      env:
-        PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
-      run: |
-        pipx install poetry
-        pipx inject poetry poetry-plugin-export
-        pipx inject poetry poetry-dynamic-versioning[plugin]
-        poetry --version
-        poetry self show plugins
-
     - uses: actions/setup-python@v5
       with:
         python-version: ${{ env.NOXPYTHON }}
@@ -152,10 +138,12 @@ jobs:
         PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
       run: |
         pipx install 'nox[uv]'
-        pipx inject nox nox-poetry
         nox --version
 
     - name: Run Nox
+      env:
+        PIP_PRE: "1"
+        UV_PRERELEASE: allow
       run: |
         nox -- -m "external"
 
@@ -167,19 +155,9 @@ jobs:
       NOXSESSION: coverage
     steps:
     - uses: actions/checkout@v4
-
-    - name: Install Poetry
-      env:
-        PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
-      run: |
-        pipx install poetry
-        pipx inject poetry poetry-plugin-export
-        poetry --version
-        poetry self show plugins
-
     - uses: actions/setup-python@v5
       with:
-        python-version: '3.12'
+        python-version: '3.x'
 
     - name: Upgrade pip
       env:
@@ -198,7 +176,6 @@ jobs:
         PIP_CONSTRAINT: ${{ github.workspace }}/.github/workflows/constraints.txt
       run: |
         pipx install 'nox[uv]'
-        pipx inject nox nox-poetry
         nox --version
 
     - run: nox --install-only
diff --git a/.github/workflows/version_bump.yml b/.github/workflows/version_bump.yml
index 7f56cfba6..ab81bb067 100644
--- a/.github/workflows/version_bump.yml
+++ b/.github/workflows/version_bump.yml
@@ -47,12 +47,11 @@ jobs:
 
     - uses: actions/setup-python@v5
       with:
-        python-version: "3.12"
-        architecture: x64
+        python-version: "3.x"
 
     - name: Bump version
       id: cz-bump
-      uses: commitizen-tools/commitizen-action@0.21.0
+      uses: commitizen-tools/commitizen-action@0.22.0
       with:
         increment: ${{ github.event.inputs.bump != 'auto' && github.event.inputs.bump || '' }}
         prerelease: ${{ github.event.inputs.prerelease != 'none' && github.event.inputs.prerelease || '' }}
@@ -102,6 +101,5 @@ jobs:
 
           [Release Draft](${{ steps.draft-release.outputs.url }})
         branch: release/v${{ steps.cz-bump.outputs.version }}
-        base: main
         labels: release
         assignees: "${{ github.actor }}"
diff --git a/.pre-commit-config.yaml b/.pre-commit-config.yaml
index 4acaba7b9..fba77db69 100644
--- a/.pre-commit-config.yaml
+++ b/.pre-commit-config.yaml
@@ -5,7 +5,7 @@ ci:
 
 repos:
 - repo: https://github.com/pre-commit/pre-commit-hooks
-  rev: v4.6.0
+  rev: v5.0.0
   hooks:
   - id: check-json
     exclude: |
@@ -35,22 +35,16 @@ repos:
         tests/snapshots/.*
       )$
   - id: trailing-whitespace
-    exclude: |
-        (?x)^(
-            .bumpversion.cfg|
-            singer_sdk/helpers/_simpleeval.py|
-            tests/core/test_simpleeval.py
-        )$
 
 - repo: https://github.com/python-jsonschema/check-jsonschema
-  rev: 0.29.3
+  rev: 0.29.4
   hooks:
   - id: check-dependabot
   - id: check-github-workflows
   - id: check-readthedocs
 
 - repo: https://github.com/astral-sh/ruff-pre-commit
-  rev: v0.6.8
+  rev: v0.7.3
   hooks:
   - id: ruff
     args: [--fix, --exit-non-zero-on-fix, --show-fixes]
diff --git a/.readthedocs.yml b/.readthedocs.yml
index 3b35af1b7..19438e79e 100644
--- a/.readthedocs.yml
+++ b/.readthedocs.yml
@@ -1,7 +1,7 @@
 version: 2
 
 build:
-  os: ubuntu-22.04
+  os: ubuntu-24.04
   tools:
     python: "3.12"
 
diff --git a/CHANGELOG.md b/CHANGELOG.md
index d28c53016..78d17d1e8 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,48 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
+## v0.42.1 (2024-11-11)
+
+### 🐛 Fixes
+
+- [#2756](https://github.com/meltano/sdk/issues/2756) Safely compare UUID replication keys with state bookmarks -- _**Thanks @nikzavada!**_
+
+## v0.42.0 (2024-11-11)
+
+### ✨ New
+
+- [#2742](https://github.com/meltano/sdk/issues/2742) Update dependencies in templates
+- [#2732](https://github.com/meltano/sdk/issues/2732) SQL target developers can now more easily override the mapping from JSON schema to SQL column type
+- [#2730](https://github.com/meltano/sdk/issues/2730) Added `SQLConnector.prepare_primary_key` for target to implement for custom table primary key adaptation
+- [#2488](https://github.com/meltano/sdk/issues/2488) Nested schema properties can now be defined as nullable
+- [#2518](https://github.com/meltano/sdk/issues/2518) Python 3.13 is officially supported
+- [#2637](https://github.com/meltano/sdk/issues/2637) Environment variables are now parsed for boolean, integer, array and object setting values
+- [#2699](https://github.com/meltano/sdk/issues/2699) Stream name can now be accessed in stream maps -- _**Thanks @holly-evans!**_
+- [#2712](https://github.com/meltano/sdk/issues/2712) JSON schema `title` is now supported in configuration and stream properties
+- [#2707](https://github.com/meltano/sdk/issues/2707) Bumped simpleeval to 1.0
+- [#2701](https://github.com/meltano/sdk/issues/2701) Stream name can now be accessed in `__alias__` context of stream maps -- _**Thanks @holly-evans!**_
+
+### 🐛 Fixes
+
+- [#2741](https://github.com/meltano/sdk/issues/2741) `datetime.datetime` instances in stream maps are now correctly mapped to `date-time` JSON schema strings
+- [#2727](https://github.com/meltano/sdk/issues/2727) Object and array JSON types are now handled before primitive types when converting them to SQL types
+- [#2723](https://github.com/meltano/sdk/issues/2723) JSON schema union types are no longer conformed into boolean values
+
+### ⚙️ Under the Hood
+
+- [#2743](https://github.com/meltano/sdk/issues/2743) Deprecate passing file paths to plugin and stream initialization
+
+### 📚 Documentation Improvements
+
+- [#2745](https://github.com/meltano/sdk/issues/2745) Document the current release process
+- [#2717](https://github.com/meltano/sdk/issues/2717) Update Meltano commands in examples
+
+### 📦 Packaging changes
+
+- [#2736](https://github.com/meltano/sdk/issues/2736) Skip `simpleeval` 1.0.1
+- [#2716](https://github.com/meltano/sdk/issues/2716) Stopped testing with SQLAlchemy 1.4
+- [#2714](https://github.com/meltano/sdk/issues/2714) Remove constraint on `urllib3`
+
 ## v0.41.0 (2024-10-02)
 
 ### ✨ New
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/build.yml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/build.yml
index 425f733a6..179acf18a 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/build.yml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/build.yml
@@ -42,4 +42,4 @@ jobs:
     - name: Publish
       ## TODO: create a trusted publisher on PyPI
       ## https://docs.pypi.org/trusted-publishers/
-      uses: pypa/gh-action-pypi-publish@v1.10.2
+      uses: pypa/gh-action-pypi-publish@v1.12.2
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/test.yml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/test.yml
index fd66735dc..4acc3b57b 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/test.yml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.github/workflows/test.yml
@@ -38,6 +38,7 @@ jobs:
         - "3.10"
         - "3.11"
         - "3.12"
+        - "3.13"
     steps:
     - uses: actions/checkout@v4
     - name: Set up Python {{ '${{ matrix.python-version }}' }}
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.pre-commit-config.yaml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.pre-commit-config.yaml
index 58f0f5b0e..e456b9896 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.pre-commit-config.yaml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/.pre-commit-config.yaml
@@ -5,7 +5,7 @@ ci:
 
 repos:
 - repo: https://github.com/pre-commit/pre-commit-hooks
-  rev: v4.6.0
+  rev: v5.0.0
   hooks:
   - id: check-json
     exclude: |
@@ -18,19 +18,19 @@ repos:
   - id: trailing-whitespace
 
 - repo: https://github.com/python-jsonschema/check-jsonschema
-  rev: 0.29.3
+  rev: 0.29.4
   hooks:
   - id: check-dependabot
   - id: check-github-workflows
 
 - repo: https://github.com/astral-sh/ruff-pre-commit
-  rev: v0.6.8
+  rev: v0.7.3
   hooks:
   - id: ruff
     args: [--fix, --exit-non-zero-on-fix, --show-fixes]
   - id: ruff-format
 
 - repo: https://github.com/pre-commit/mirrors-mypy
-  rev: v1.11.2
+  rev: v1.13.0
   hooks:
   - id: mypy
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
index 919a92dc6..f09be6d50 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/pyproject.toml
@@ -20,6 +20,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
@@ -30,12 +31,12 @@ packages = [
 
 [tool.poetry.dependencies]
 python = ">=3.9"
-singer-sdk = { version="~=0.41.0"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
+singer-sdk = { version="~=0.42.1"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
 fs-s3fs = { version = "~=1.1.1", optional = true }
 
 [tool.poetry.group.dev.dependencies]
 pytest = ">=8"
-singer-sdk = { version="~=0.41.0", extras = ["testing"] }
+singer-sdk = { version="~=0.42.1", extras = ["testing"] }
 
 [tool.poetry.extras]
 s3 = ["fs-s3fs"]
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/{{cookiecutter.library_name}}/mapper.py b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/{{cookiecutter.library_name}}/mapper.py
index 8e6ea991e..af6406201 100644
--- a/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/{{cookiecutter.library_name}}/mapper.py
+++ b/cookiecutter/mapper-template/{{cookiecutter.mapper_id}}/{{cookiecutter.library_name}}/mapper.py
@@ -23,6 +23,7 @@ class {{ cookiecutter.name }}Mapper(InlineMapper):
         th.Property(
             "example_config",
             th.StringType,
+            title="Example Configuration",
             description="An example config, replace or remove based on your needs.",
         ),
     ).to_dict()
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/build.yml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/build.yml
index 425f733a6..179acf18a 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/build.yml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/build.yml
@@ -42,4 +42,4 @@ jobs:
     - name: Publish
       ## TODO: create a trusted publisher on PyPI
       ## https://docs.pypi.org/trusted-publishers/
-      uses: pypa/gh-action-pypi-publish@v1.10.2
+      uses: pypa/gh-action-pypi-publish@v1.12.2
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/test.yml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/test.yml
index ed9549bca..380e39371 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/test.yml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.github/workflows/test.yml
@@ -38,6 +38,7 @@ jobs:
         - "3.10"
         - "3.11"
         - "3.12"
+        - "3.13"
     steps:
     - uses: actions/checkout@v4
     - name: Set up Python {{ '${{ matrix.python-version }}' }}
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.pre-commit-config.yaml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.pre-commit-config.yaml
index 4acde2515..869ab2492 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.pre-commit-config.yaml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/.pre-commit-config.yaml
@@ -5,7 +5,7 @@ ci:
 
 repos:
 - repo: https://github.com/pre-commit/pre-commit-hooks
-  rev: v4.6.0
+  rev: v5.0.0
   hooks:
   - id: check-json
     exclude: |
@@ -18,20 +18,20 @@ repos:
   - id: trailing-whitespace
 
 - repo: https://github.com/python-jsonschema/check-jsonschema
-  rev: 0.29.3
+  rev: 0.29.4
   hooks:
   - id: check-dependabot
   - id: check-github-workflows
 
 - repo: https://github.com/astral-sh/ruff-pre-commit
-  rev: v0.6.8
+  rev: v0.7.3
   hooks:
   - id: ruff
     args: [--fix, --exit-non-zero-on-fix, --show-fixes]
   - id: ruff-format
 
 - repo: https://github.com/pre-commit/mirrors-mypy
-  rev: v1.11.2
+  rev: v1.13.0
   hooks:
   - id: mypy
     additional_dependencies:
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
index 38ef2b94f..bf1deb719 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/pyproject.toml
@@ -19,6 +19,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
@@ -29,7 +30,7 @@ packages = [
 
 [tool.poetry.dependencies]
 python = ">=3.9"
-singer-sdk = { version="~=0.41.0", extras = [
+singer-sdk = { version="~=0.42.1", extras = [
     {%- if cookiecutter.auth_method == "JWT" -%}"jwt", {% endif -%}
     {%- if cookiecutter.faker_extra -%}"faker",{%- endif -%}
 ] }
@@ -41,9 +42,9 @@ requests = "~=2.32.3"
 [tool.poetry.group.dev.dependencies]
 pytest = ">=8"
 {%- if cookiecutter.auth_method == "JWT" %}
-singer-sdk = { version="~=0.41.0", extras = ["jwt", "testing"] }
+singer-sdk = { version="~=0.42.1", extras = ["jwt", "testing"] }
 {%- else %}
-singer-sdk = { version="~=0.41.0", extras = ["testing"] }
+singer-sdk = { version="~=0.42.1", extras = ["testing"] }
 {%- endif %}
 
 [tool.poetry.extras]
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/graphql-client.py b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/graphql-client.py
index d1289efa4..289199b11 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/graphql-client.py
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/graphql-client.py
@@ -45,14 +45,11 @@ def http_headers(self) -> dict:
         Returns:
             A dictionary of HTTP headers.
         """
-        headers = {}
-        if "user_agent" in self.config:
-            headers["User-Agent"] = self.config.get("user_agent")
 {%- if cookiecutter.auth_method not in ("OAuth2", "JWT") %}
         # If not using an authenticator, you may also provide inline auth headers:
         # headers["Private-Token"] = self.config.get("auth_token")
 {%- endif %}
-        return headers
+        return {}
 
     def parse_response(self, response: requests.Response) -> t.Iterable[dict]:
         """Parse the response and return an iterator of result records.
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/other-client.py b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/other-client.py
index bf7e2536d..6564b4926 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/other-client.py
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/other-client.py
@@ -15,7 +15,7 @@ class {{ cookiecutter.source_name }}Stream(Stream):
 
     def get_records(
         self,
-        context: Context | None,  # noqa: ARG002
+        context: Context | None,
     ) -> t.Iterable[dict]:
         """Return a generator of record-type dictionary objects.
 
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/rest-client.py b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/rest-client.py
index c1aa634a5..35a53303c 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/rest-client.py
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/rest-client.py
@@ -132,14 +132,11 @@ def http_headers(self) -> dict:
         Returns:
             A dictionary of HTTP headers.
         """
-        headers = {}
-        if "user_agent" in self.config:
-            headers["User-Agent"] = self.config.get("user_agent")
 {%- if cookiecutter.auth_method not in ("OAuth2", "JWT") %}
         # If not using an authenticator, you may also provide inline auth headers:
         # headers["Private-Token"] = self.config.get("auth_token")  # noqa: ERA001
 {%- endif %}
-        return headers
+        return {}
 
     def get_new_paginator(self) -> BaseAPIPaginator:
         """Create a new pagination helper instance.
diff --git a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/tap.py b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/tap.py
index 74c8927e9..3fbd58a43 100644
--- a/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/tap.py
+++ b/cookiecutter/tap-template/{{cookiecutter.tap_id}}/{{cookiecutter.library_name}}/tap.py
@@ -31,12 +31,14 @@ class Tap{{ cookiecutter.source_name }}({{ 'SQL' if cookiecutter.stream_type ==
             th.StringType,
             required=True,
             secret=True,  # Flag config as protected.
+            title="Auth Token",
             description="The token to authenticate against the API service",
         ),
         th.Property(
             "project_ids",
             th.ArrayType(th.StringType),
             required=True,
+            title="Project IDs",
             description="Project IDs to replicate",
         ),
         th.Property(
@@ -47,6 +49,7 @@ class Tap{{ cookiecutter.source_name }}({{ 'SQL' if cookiecutter.stream_type ==
         th.Property(
             "api_url",
             th.StringType,
+            title="API URL",
             default="https://api.mysample.com",
             description="The url for the API service",
         ),
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/build.yml b/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/build.yml
index 425f733a6..179acf18a 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/build.yml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/build.yml
@@ -42,4 +42,4 @@ jobs:
     - name: Publish
       ## TODO: create a trusted publisher on PyPI
       ## https://docs.pypi.org/trusted-publishers/
-      uses: pypa/gh-action-pypi-publish@v1.10.2
+      uses: pypa/gh-action-pypi-publish@v1.12.2
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/test.yml b/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/test.yml
index 9a098a000..db8a39d17 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/test.yml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/.github/workflows/test.yml
@@ -38,6 +38,7 @@ jobs:
         - "3.10"
         - "3.11"
         - "3.12"
+        - "3.13"
     steps:
     - uses: actions/checkout@v4
     - name: Set up Python {{ '${{ matrix.python-version }}' }}
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/.pre-commit-config.yaml b/cookiecutter/target-template/{{cookiecutter.target_id}}/.pre-commit-config.yaml
index 13e74461c..86aedf0e9 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/.pre-commit-config.yaml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/.pre-commit-config.yaml
@@ -5,7 +5,7 @@ ci:
 
 repos:
 - repo: https://github.com/pre-commit/pre-commit-hooks
-  rev: v4.6.0
+  rev: v5.0.0
   hooks:
   - id: check-json
     exclude: |
@@ -18,20 +18,20 @@ repos:
   - id: trailing-whitespace
 
 - repo: https://github.com/python-jsonschema/check-jsonschema
-  rev: 0.29.3
+  rev: 0.29.4
   hooks:
   - id: check-dependabot
   - id: check-github-workflows
 
 - repo: https://github.com/astral-sh/ruff-pre-commit
-  rev: v0.6.8
+  rev: v0.7.3
   hooks:
   - id: ruff
     args: [--fix, --exit-non-zero-on-fix, --show-fixes]
   - id: ruff-format
 
 - repo: https://github.com/pre-commit/mirrors-mypy
-  rev: v1.11.2
+  rev: v1.13.0
   hooks:
   - id: mypy
     additional_dependencies:
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
index 27cb43531..6074b71bc 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml
@@ -19,6 +19,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 {%- if cookiecutter.variant != "None (Skip)" %}
@@ -29,7 +30,7 @@ packages = [
 
 [tool.poetry.dependencies]
 python = ">=3.9"
-singer-sdk = { version="~=0.41.0"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
+singer-sdk = { version="~=0.42.1"{{ ', extras = ["faker"]' if cookiecutter.faker_extra }} }
 fs-s3fs = { version = "~=1.1.1", optional = true }
 {%- if cookiecutter.serialization_method != "SQL" %}
 requests = "~=2.32.3"
@@ -37,7 +38,7 @@ requests = "~=2.32.3"
 
 [tool.poetry.dev-dependencies]
 pytest = ">=8"
-singer-sdk = { version="~=0.41.0", extras = ["testing"] }
+singer-sdk = { version="~=0.42.1", extras = ["testing"] }
 
 [tool.poetry.extras]
 s3 = ["fs-s3fs"]
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
index fb5b1cf87..90c122a54 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py3{9,10,11,12}
+envlist = py3{9,10,11,12,13}
 requires =
     tox>=4.19
 
diff --git a/cookiecutter/target-template/{{cookiecutter.target_id}}/{{cookiecutter.library_name}}/target.py b/cookiecutter/target-template/{{cookiecutter.target_id}}/{{cookiecutter.library_name}}/target.py
index f28bb4e94..e66a10eae 100644
--- a/cookiecutter/target-template/{{cookiecutter.target_id}}/{{cookiecutter.library_name}}/target.py
+++ b/cookiecutter/target-template/{{cookiecutter.target_id}}/{{cookiecutter.library_name}}/target.py
@@ -23,23 +23,27 @@ class Target{{ cookiecutter.destination_name }}({{ target_class }}):
             "sqlalchemy_url",
             th.StringType,
             secret=True,  # Flag config as protected.
+            title="SQLAlchemy URL",
             description="SQLAlchemy connection string",
         ),
         {%- else %}
         th.Property(
             "filepath",
             th.StringType,
+            title="Output File Path",
             description="The path to the target output file",
         ),
         th.Property(
             "file_naming_scheme",
             th.StringType,
+            title="File Naming Scheme",
             description="The scheme with which output files will be named",
         ),
         th.Property(
             "auth_token",
             th.StringType,
             secret=True,  # Flag config as protected.
+            title="Auth Token",
             description="The path to the target output file",
         ),
         {%- endif %}
diff --git a/docs/CONTRIBUTING.md b/docs/CONTRIBUTING.md
index d147d775a..29a5eee82 100644
--- a/docs/CONTRIBUTING.md
+++ b/docs/CONTRIBUTING.md
@@ -30,7 +30,6 @@ With `pipx` installed, you globally add the required tools:
 pipx install poetry
 pipx install pre-commit
 pipx install nox
-pipx inject nox nox-poetry
 ```
 
 Now you can use Poetry to install package dependencies:
diff --git a/docs/_templates/stream_class.rst b/docs/_templates/stream_class.rst
new file mode 100644
index 000000000..547bd6454
--- /dev/null
+++ b/docs/_templates/stream_class.rst
@@ -0,0 +1,10 @@
+{{ fullname }}
+{{ "=" * fullname|length }}
+
+.. currentmodule:: {{ module }}
+
+.. autoclass:: {{ name }}
+    :members:
+    :show-inheritance:
+    :inherited-members: Stream
+    :special-members: __init__
diff --git a/docs/classes/singer_sdk.GraphQLStream.rst b/docs/classes/singer_sdk.GraphQLStream.rst
index 41953196f..2e801b64b 100644
--- a/docs/classes/singer_sdk.GraphQLStream.rst
+++ b/docs/classes/singer_sdk.GraphQLStream.rst
@@ -5,4 +5,6 @@
 
 .. autoclass:: GraphQLStream
     :members:
-    :special-members: __init__, __call__
\ No newline at end of file
+    :show-inheritance:
+    :inherited-members: Stream
+    :special-members: __init__
\ No newline at end of file
diff --git a/docs/classes/singer_sdk.RESTStream.rst b/docs/classes/singer_sdk.RESTStream.rst
index 9710c6303..6ed4d7b47 100644
--- a/docs/classes/singer_sdk.RESTStream.rst
+++ b/docs/classes/singer_sdk.RESTStream.rst
@@ -5,4 +5,6 @@
 
 .. autoclass:: RESTStream
     :members:
-    :special-members: __init__, __call__
\ No newline at end of file
+    :show-inheritance:
+    :inherited-members: Stream
+    :special-members: __init__
\ No newline at end of file
diff --git a/docs/classes/singer_sdk.SQLStream.rst b/docs/classes/singer_sdk.SQLStream.rst
index f72894088..bc0546f31 100644
--- a/docs/classes/singer_sdk.SQLStream.rst
+++ b/docs/classes/singer_sdk.SQLStream.rst
@@ -5,4 +5,6 @@
 
 .. autoclass:: SQLStream
     :members:
-    :special-members: __init__, __call__
\ No newline at end of file
+    :show-inheritance:
+    :inherited-members: Stream
+    :special-members: __init__
\ No newline at end of file
diff --git a/docs/classes/singer_sdk.Stream.rst b/docs/classes/singer_sdk.Stream.rst
index db028a912..946f040d6 100644
--- a/docs/classes/singer_sdk.Stream.rst
+++ b/docs/classes/singer_sdk.Stream.rst
@@ -5,4 +5,6 @@
 
 .. autoclass:: Stream
     :members:
-    :special-members: __init__, __call__
\ No newline at end of file
+    :show-inheritance:
+    :inherited-members: Stream
+    :special-members: __init__
\ No newline at end of file
diff --git a/docs/classes/singer_sdk.connectors.sql.JSONSchemaToSQL.rst b/docs/classes/singer_sdk.connectors.sql.JSONSchemaToSQL.rst
new file mode 100644
index 000000000..82ad1c544
--- /dev/null
+++ b/docs/classes/singer_sdk.connectors.sql.JSONSchemaToSQL.rst
@@ -0,0 +1,8 @@
+singer_sdk.connectors.sql.JSONSchemaToSQL
+=========================================
+
+.. currentmodule:: singer_sdk.connectors.sql
+
+.. autoclass:: JSONSchemaToSQL
+    :members:
+    :special-members: __init__, __call__
\ No newline at end of file
diff --git a/docs/cli_commands.md b/docs/cli_commands.md
index d12d245f8..e5d37f551 100644
--- a/docs/cli_commands.md
+++ b/docs/cli_commands.md
@@ -180,7 +180,7 @@ plugins:
 | Configuration store | Config JSON file (`--config=path/to/config.json`) or environment variables (`--config=ENV`) | `meltano.yml`, `.env`, environment variables, or Meltano's system db |
 | Simple invocation   | `my-tap --config=...`                                                                       | `meltano invoke my-tap`                                              |
 | Other CLI options   | `my-tap --about --format=json`                                                              | `meltano invoke my-tap --about --format=json`                        |
-| ELT                 | `my-tap --config=... \| path/to/target-jsonl --config=...`                                  | `meltano elt my-tap target-jsonl`                                    |
+| ELT                 | `my-tap --config=... \| path/to/target-jsonl --config=...`                                  | `meltano run my-tap target-jsonl`                                    |
 
 [Meltano]: https://www.meltano.com
 [declare settings]: https://docs.meltano.com/reference/command-line-interface#how-to-use-2
diff --git a/docs/conf.py b/docs/conf.py
index f2ee91c7a..48a83cd8c 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -29,7 +29,7 @@
 author = "Meltano Core Team and Contributors"
 
 # The full version, including alpha/beta/rc tags
-release = "0.41.0"
+release = "0.42.1"
 
 
 # -- General configuration -------------------------------------------------------------
diff --git a/docs/guides/config-schema.md b/docs/guides/config-schema.md
index e5aad4378..d4ea1d16b 100644
--- a/docs/guides/config-schema.md
+++ b/docs/guides/config-schema.md
@@ -15,9 +15,9 @@ class MyTap(Tap):
     name = "my-tap"
 
     config_jsonschema = th.PropertiesList(
-        th.Property("api_key", th.StringType, required=True),
-        th.Property("base_url", th.StringType, default="https://api.example.com"),
-        th.Property("start_date", th.DateTimeType),
+        th.Property("api_key", th.StringType, required=True, title="API Key"),
+        th.Property("base_url", th.StringType, default="https://api.example.com", title="Base URL"),
+        th.Property("start_date", th.DateTimeType, title="Start Date"),
     ).to_dict()
 ```
 
@@ -29,6 +29,7 @@ Explanation of the configuration schema defined above:
 - The `th.StringType`, `th.DateTimeType`, etc. helpers are used to define the type of the property.
 - The `required` attribute is used to mark a property as required. The tap will throw an error if the user does not provide a value for a required property.
 - The `default` attribute is used to provide a default value for a property. The tap will use this if the user does not provide a value, so this can be accessed in the tap or streams with square bracket syntax, i.e. `self.config["base_url"]`.
+- The `title` attribute is used to provide a human-readable title for the property.
 - The `to_dict()` method is used to convert the JSON object to a Python dictionary.
 
 See the full reference for the [typing module](../typing.rst) for more information on how to define a configuration schema.
diff --git a/docs/guides/index.md b/docs/guides/index.md
index 60a94e8d5..f754908a2 100644
--- a/docs/guides/index.md
+++ b/docs/guides/index.md
@@ -10,4 +10,5 @@ pagination-classes
 custom-clis
 config-schema
 sql-tap
+sql-target
 ```
diff --git a/docs/guides/sql-target.md b/docs/guides/sql-target.md
new file mode 100644
index 000000000..7a9930a2a
--- /dev/null
+++ b/docs/guides/sql-target.md
@@ -0,0 +1,52 @@
+# Building SQL targets
+
+## Mapping JSON Schema to SQL types
+
+Starting with version `0.42.0`, the Meltano Singer SDK provides a clean way to map JSON Schema to SQL types. This is useful when the SQL dialect needs to do special handling for certain JSON Schema types.
+
+### Custom JSON Schema mapping
+
+If the default [`JSONSchemaToSQL`](connectors.sql.JSONSchemaToSQL) instance doesn't cover all the types supported by the SQLAlchemy dialect in your target, you can override the {attr}`SQLConnector.jsonschema_to_sql <singer_sdk.SQLConnector.jsonschema_to_sql>` property and register a new type handler for the type you need to support:
+
+```python
+import functools
+
+import sqlalchemy as sa
+from singer_sdk import typing as th
+from singer_sdk.connectors import JSONSchemaToSQL, SQLConnector
+
+from my_sqlalchemy_dialect import VectorType
+
+
+def custom_array_to_sql(jsonschema: dict) -> VectorType | sa.types.VARCHAR:
+    """Custom mapping for arrays of numbers."""
+    if items := jsonschema.get("items"):
+        if items.get("type") == "number":
+            return VectorType()
+
+    return sa.types.VARCHAR()
+
+
+class MyConnector(SQLConnector):
+    @functools.cached_property
+    def jsonschema_to_sql(self):
+        to_sql = JSONSchemaToSQL()
+        to_sql.register_type_handler("array", custom_array_to_sql)
+        return to_sql
+```
+
+### Custom string format mapping
+
+You can also register a new format handler for custom string formats:
+
+```python
+from my_sqlalchemy_dialect import URI
+
+
+class MyConnector(SQLConnector):
+    @functools.cached_property
+    def jsonschema_to_sql(self):
+        to_sql = JSONSchemaToSQL()
+        to_sql.register_format_handler("uri", URI)
+        return to_sql
+```
diff --git a/docs/implementation/cli.md b/docs/implementation/cli.md
index e4f78c26b..92d77fa37 100644
--- a/docs/implementation/cli.md
+++ b/docs/implementation/cli.md
@@ -1,5 +1,4 @@
 ---
-# TODO: this will be supported after MyST-Parser 0.18.0 is released
 myst:
   heading_anchors: 4
 ---
@@ -69,9 +68,19 @@ values from environment variables, and from a `.env` file if present within the
 working directory, which match the exact name of a setting, along with a prefix determined
 by the plugin name.
 
-> For example: For a sample plugin named `tap-my-example` and settings named "username" and "access_key", the SDK will automatically scrape
-> the settings from environment variables `TAP_MY_EXAMPLE_USERNAME` and
-> `TAP_MY_EXAMPLE_ACCESS_KEY`, if they exist.
+```{note}
+For example, for a sample plugin named `tap-my-example` and settings named `username` and `access_key`, the SDK will automatically scrape
+the settings from environment variables `TAP_MY_EXAMPLE_USERNAME` and
+`TAP_MY_EXAMPLE_ACCESS_KEY` respectively, if they exist.
+```
+
+The following value types are automatically cast to the appropriate Python type:
+
+- integer (e.g. `TAP_MY_EXAMPLE_PORT=5432`)
+- boolean (e.g. `TAP_MY_EXAMPLE_DEBUG=true`)
+- JSON arrays (e.g. `TAP_MY_EXAMPLE_ARRAY='["a", "b", "c"]'`)
+- JSON objects (e.g. `TAP_MY_EXAMPLE_OBJECT='{"key": "value"}'`)
+
 
 ## Tap-Specific CLI Options
 
diff --git a/docs/reference.rst b/docs/reference.rst
index eeaf1b53a..6522c8a36 100644
--- a/docs/reference.rst
+++ b/docs/reference.rst
@@ -21,7 +21,7 @@ Stream Classes
 
 .. autosummary::
     :toctree: classes
-    :template: class.rst
+    :template: stream_class.rst
 
     Stream
     RESTStream
@@ -152,3 +152,4 @@ Other
     :template: class.rst
 
     connectors.sql.SQLToJSONSchema
+    connectors.sql.JSONSchemaToSQL
diff --git a/docs/release_process.md b/docs/release_process.md
index 2163e4db8..131ef9075 100644
--- a/docs/release_process.md
+++ b/docs/release_process.md
@@ -1,29 +1,64 @@
+---
+myst:
+  heading_anchors: 4
+---
+
 # Release Process
 
+The Singer SDK currently follows roughly a [ZeroVer versioning scheme](https://0ver.org/). Starting with the Singer SDK 1.0, version numbers will use [semantic versioning](https://semver.org/).
+
 ## PyPI releases
 
-Releases are published to PyPI by a GitHub Actions workflow, triggered when a GitHub [Release](https://github.com/meltano/sdk/releases) is published.
+### Stable releases
+
+The following steps are required to create a stable release:
+
+1. Trigger the `.github/workflows/version_bump.yml` workflow from the GitHub Actions tab, or from the CLI with `gh workflow run version_bump.yml`.
+2. Wait for the workflow to complete. It will create a new PR with the version bump, and also a draft release.
+3. Review the PR for any errors in the changelog and version bumps, then merge it.
+4. Publish the draft release from the GitHub Releases tab.
 
-### Feature releases
+#### Feature releases
 
 Feature releases are the primary way that new features are added to the Singer SDK. They are released on a roughly monthly cadence.
 
-### Patch releases
+#### Patch releases
 
 Patch releases are released as needed to fix bugs or security issues. They are released on an as-needed basis.
 
-## Release cadence
+#### Release Highlights
+
+Once the release is published, we manually add a section to the changelog with the release highlights. This section should include a brief description of the most important changes in the release. For example:
+
+```markdown
+## v0.41.0 (2024-10-02)
+
+### Highlights
 
-Starting with the Singer SDK 1.0, version numbers will use a loose form of [semantic versioning](https://semver.org/).
+- It's easier now for SQL tap developers to customize the mapping from SQL column types to JSON schema. See [the guide](https://sdk.meltano.com/en/v0.41.0/guides/sql-tap.html#custom-type-mapping) for details.
+```
+
+### Pre-releases
+
+```bash
+git tag v0.42.0a3
+git push origin v0.42.0a3
+```
+
+Pre-releases are normal tags with pre-release identifiers. They are used to test new features before a stable release. Pre-releases are triggered by pushing a tag with a pre-release identifier, e.g. `v0.42.0a3`.
+
+We don't generate release notes for pre-releases, nor do we update the changelog so creating a pre-release is as simple as pushing a tag:
+
+## Release cadence
 
-SemVer makes it easier to see at a glance how compatible releases are with each other. It also helps to anticipate when compatibility shims will be removed.
+The Singer SDK follows a roughly monthly release cadence. [Milestones](https://github.com/meltano/sdk/milestones) are used to track the progress of each release. The milestones are named after the release version, e.g. `v0.42.0`.
 
 ## Deprecation policy
 
 A [feature release](#feature-releases) may deprecate a feature, but it will not remove it until the next major release. A deprecation will be clearly documented in the changelog and in the code.
 
-All deprecated features will emit a `SingerDeprecationWarning` when used, so users can raise them as exceptions when running their tests to ensure that they are not using any deprecated features:
+All deprecated features will emit a `SingerSDKDeprecationWarning` when used, so users can raise them as exceptions when running their tests to ensure that they are not using any deprecated features:
 
 ```console
-$ pytest -W error::singer_sdk.utils.deprecation.SingerSDKDeprecationWarning
+$ pytest -W error::singer_sdk.helpers._compat.SingerSDKDeprecationWarning
 ```
diff --git a/docs/stream_maps.md b/docs/stream_maps.md
index e31a9b634..a47539158 100644
--- a/docs/stream_maps.md
+++ b/docs/stream_maps.md
@@ -228,30 +228,29 @@ can be referenced directly by mapping expressions.
 
 #### Built-In Functions
 
-- [`md5()`](inv:python:py:module:#hashlib) - returns an inline MD5 hash of any string, outputting
-    the string representation of the hash's hex digest.
-  - This is defined by the SDK internally with native python:
-    [`hashlib.md5(<input>.encode("utf-8")).hexdigest()`](inv:python:py:method:#hashlib.hash.hexdigest).
-- [`datetime`](inv:python:py:module:#datetime) - This is the datetime module object from the Python
-    standard library. You can access [`datetime.datetime`](inv:python:py:class:#datetime.datetime),
-    [`datetime.timedelta`](inv:python:py:class:#datetime.timedelta), etc.
-- [`json`](inv:python:py:module:#json) - This is the json module object from the Python standard
-    library. Primarily used for calling [`json.dumps()`](inv:python:py:function:#json.dumps)
-    and [`json.loads()`](inv:python:py:function:#json.loads).
+The following functions and namespaces are available for use in mapping expressions:
+
+| Function                                     | Description                                                                                                                                                                                                                                                            |
+| :------------------------------------------- | :--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- |
+| [`md5()`](inv:python:py:module:#hashlib)     | Returns an inline MD5 hash of any string, outputting the string representation of the hash's hex digest. This is defined by the SDK internally with native python: [`hashlib.md5(<input>.encode("utf-8")).hexdigest()`](inv:python:py:method:#hashlib.hash.hexdigest). |
+| [`datetime`](inv:python:py:module:#datetime) | This is the datetime module object from the Python standard library. You can access [`datetime.datetime`](inv:python:py:class:#datetime.datetime), [`datetime.timedelta`](inv:python:py:class:#datetime.timedelta), etc.                                               |
+| [`json`](inv:python:py:module:#json)         | This is the json module object from the Python standard library. Primarily used for calling [`json.dumps()`](inv:python:py:function:#json.dumps) and [`json.loads()`](inv:python:py:function:#json.loads).                                                             |
 
 #### Built-in Variable Names
 
-- `config` - a dictionary with the `stream_map_config` values from settings. This can be used
-  to provide a secret hash seed, for instance.
-- `record` - an alias for the record values dictionary in the current stream.
-- `_` - same as `record` but shorter to type
-- `self` - the existing property value if the property already exists
-- `fake` - a [`Faker`](inv:faker:std:doc#index) instance, configurable via `faker_config`
-  (see previous example) - see the built-in [standard providers](inv:faker:std:doc#providers)
-  for available methods
+The following variables are available in the context of a mapping expression:
+
+| Variable          | Description                                                                                                                                                                                       |
+| :---------------- | :------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ |
+| `config`          | A dictionary with the `stream_map_config` values from settings. This can be used to provide a secret hash seed, for instance.                                                                     |
+| `record`          | An alias for the record values dictionary in the current stream.                                                                                                                                  |
+| `_`               | Same as `record` but shorter to type.                                                                                                                                                             |
+| `self`            | The existing property value if the property already exists.                                                                                                                                       |
+| `fake`            | A [`Faker`](inv:faker:std:doc#index) instance, configurable via `faker_config` (see previous example) - see the built-in [standard providers](inv:faker:std:doc#providers) for available methods. |
+| `__stream_name__` | The name of the stream. Useful when [applying the same transformation to multiple streams](#applying-a-mapping-across-two-or-more-streams).                                                       |
 
   ```{tip}
-  The `fake` object is only available if the plugin specifies `faker` as an additional dependency (through the `singer-sdk` `faker` extra, or directly).
+  To use the `fake` object, the `faker` library must be installed.
   ```
 
 :::{versionadded} 0.35.0
@@ -262,10 +261,26 @@ The `faker` object.
 The `Faker` class.
 :::
 
-:::{versionchanged} TODO
+:::{versionchanged} 0.41.0
 The `Faker` class was deprecated in favor of instance methods on the `fake` object.
 :::
 
+:::{versionadded} 0.42.0
+The `__stream_name__` variable.
+:::
+
+#### Built-in Alias Variable Names
+
+The following variables are available in the context of the `__alias__` expression:
+
+| Variable          | Description              |
+| :---------------- | :----------------------- |
+| `__stream_name__` | The existing stream name |
+
+:::{versionadded} 0.42.0
+The `__stream_name__` variable.
+:::
+
 #### Automatic Schema Detection
 
 For performance reasons, type detection is performed at runtime using text analysis
@@ -640,6 +655,36 @@ stream_maps:
 Support for stream glob expressions.
 :::
 
+### Aliasing two or more streams
+
+The `__alias__` operation evaluates simple python expressions.
+
+You can combine this with glob expressions to rename more than one stream:
+
+````{tab} meltano.yml
+```yaml
+stream_maps:
+  "*":
+    __alias__: "__stream_name__ + '_v2'"
+```
+````
+
+````{tab} JSON
+```json
+{
+    "stream_maps": {
+        "*": {
+            "__alias__": "__stream_name__ + '_v2'"
+        }
+    }
+}
+```
+````
+
+:::{versionadded} 0.42.0
+Support for `__alias__` expression evaluation.
+:::
+
 ### Understanding Filters' Affects on Parent-Child Streams
 
 Nested child streams iterations will be skipped if their parent stream has a record-level
diff --git a/noxfile.py b/noxfile.py
index a07c953ab..8e5d667fe 100644
--- a/noxfile.py
+++ b/noxfile.py
@@ -6,20 +6,11 @@
 import shutil
 import sys
 import tempfile
+import typing as t
 from pathlib import Path
-from textwrap import dedent
 
 import nox
 
-try:
-    from nox_poetry import Session, session
-except ImportError:
-    message = f"""\
-    Nox failed to import the 'nox-poetry' package.
-    Please install it using the following command:
-    {sys.executable} -m pip install nox-poetry"""
-    raise SystemExit(dedent(message)) from None
-
 nox.needs_version = ">=2024.4.15"
 nox.options.default_venv_backend = "uv|virtualenv"
 
@@ -33,8 +24,14 @@
 COOKIECUTTER_REPLAY_FILES = list(Path("./e2e-tests/cookiecutters").glob("*.json"))
 
 package = "singer_sdk"
-python_versions = ["3.12", "3.11", "3.10", "3.9", "3.8"]
-main_python_version = "3.12"
+python_versions = [
+    "3.13",
+    "3.12",
+    "3.11",
+    "3.10",
+    "3.9",
+]
+main_python_version = "3.13"
 locations = "singer_sdk", "tests", "noxfile.py", "docs/conf.py"
 nox.options.sessions = (
     "mypy",
@@ -45,12 +42,12 @@
 )
 
 poetry_config = nox.project.load_toml("pyproject.toml")["tool"]["poetry"]
-test_dependencies = poetry_config["group"]["dev"]["dependencies"].keys()
+test_dependencies: dict[str, t.Any] = poetry_config["group"]["dev"]["dependencies"]
 typing_dependencies = poetry_config["group"]["typing"]["dependencies"].keys()
 
 
-@session(python=main_python_version)
-def mypy(session: Session) -> None:
+@nox.session(python=main_python_version)
+def mypy(session: nox.Session) -> None:
     """Check types with mypy."""
     args = session.posargs or ["singer_sdk"]
     session.install(".[faker,jwt,parquet,s3,testing]")
@@ -60,19 +57,18 @@ def mypy(session: Session) -> None:
         session.run("mypy", f"--python-executable={sys.executable}", "noxfile.py")
 
 
-@session(python=python_versions)
-def tests(session: Session) -> None:
+@nox.session(python=python_versions)
+def tests(session: nox.Session) -> None:
     """Execute pytest tests and compute coverage."""
-    session.install(".[faker,jwt,parquet,s3]")
-    session.install(*test_dependencies)
+    extras = [
+        "faker",
+        "jwt",
+        "parquet",
+        "s3",
+    ]
 
-    sqlalchemy_version = os.environ.get("SQLALCHEMY_VERSION")
-    if sqlalchemy_version:
-        # Bypass nox-poetry use of --constraint so we can install a version of
-        # SQLAlchemy that doesn't match what's in poetry.lock.
-        session.poetry.session.install(  # type: ignore[attr-defined]
-            f"sqlalchemy=={sqlalchemy_version}.*",
-        )
+    session.install(f".[{','.join(extras)}]")
+    session.install(*test_dependencies)
 
     env = {"COVERAGE_CORE": "sysmon"} if session.python == "3.12" else {}
 
@@ -93,18 +89,11 @@ def tests(session: Session) -> None:
             session.notify("coverage", posargs=[])
 
 
-@session(python=main_python_version)
-def benches(session: Session) -> None:
+@nox.session(python=main_python_version)
+def benches(session: nox.Session) -> None:
     """Run benchmarks."""
     session.install(".[jwt,s3]")
     session.install(*test_dependencies)
-    sqlalchemy_version = os.environ.get("SQLALCHEMY_VERSION")
-    if sqlalchemy_version:
-        # Bypass nox-poetry use of --constraint so we can install a version of
-        # SQLAlchemy that doesn't match what's in poetry.lock.
-        session.poetry.session.install(  # type: ignore[attr-defined]
-            f"sqlalchemy=={sqlalchemy_version}",
-        )
     session.run(
         "pytest",
         "--benchmark-only",
@@ -113,16 +102,16 @@ def benches(session: Session) -> None:
     )
 
 
-@session(name="deps", python=python_versions)
-def dependencies(session: Session) -> None:
+@nox.session(name="deps", python=main_python_version)
+def dependencies(session: nox.Session) -> None:
     """Check issues with dependencies."""
     session.install(".[s3,testing]")
     session.install("deptry")
     session.run("deptry", "singer_sdk", *session.posargs)
 
 
-@session(python=main_python_version)
-def update_snapshots(session: Session) -> None:
+@nox.session(python=main_python_version)
+def update_snapshots(session: nox.Session) -> None:
     """Update pytest snapshots."""
     args = session.posargs or ["-m", "snapshot"]
 
@@ -131,8 +120,8 @@ def update_snapshots(session: Session) -> None:
     session.run("pytest", "--snapshot-update", *args)
 
 
-@session(python=python_versions)
-def doctest(session: Session) -> None:
+@nox.session(python=python_versions)
+def doctest(session: nox.Session) -> None:
     """Run examples with xdoctest."""
     if session.posargs:
         args = [package, *session.posargs]
@@ -146,8 +135,8 @@ def doctest(session: Session) -> None:
     session.run("pytest", "--xdoctest", *args)
 
 
-@session(python=main_python_version)
-def coverage(session: Session) -> None:
+@nox.session(python=main_python_version)
+def coverage(session: nox.Session) -> None:
     """Generate coverage report."""
     args = session.posargs or ["report", "-m"]
 
@@ -159,8 +148,8 @@ def coverage(session: Session) -> None:
     session.run("coverage", *args)
 
 
-@session(name="docs", python=main_python_version)
-def docs(session: Session) -> None:
+@nox.session(name="docs", python=main_python_version)
+def docs(session: nox.Session) -> None:
     """Build the documentation."""
     args = session.posargs or ["docs", "build", "-W"]
     if not session.posargs and "FORCE_COLOR" in os.environ:
@@ -175,8 +164,8 @@ def docs(session: Session) -> None:
     session.run("sphinx-build", *args)
 
 
-@session(name="docs-serve", python=main_python_version)
-def docs_serve(session: Session) -> None:
+@nox.session(name="docs-serve", python=main_python_version)
+def docs_serve(session: nox.Session) -> None:
     """Build the documentation."""
     args = session.posargs or [
         "--open-browser",
@@ -198,8 +187,8 @@ def docs_serve(session: Session) -> None:
 
 
 @nox.parametrize("replay_file_path", COOKIECUTTER_REPLAY_FILES)
-@session(python=main_python_version)
-def test_cookiecutter(session: Session, replay_file_path: str) -> None:
+@nox.session(python=main_python_version)
+def test_cookiecutter(session: nox.Session, replay_file_path: str) -> None:
     """Uses the tap template to build an empty cookiecutter.
 
     Runs the lint task on the created test project.
@@ -261,8 +250,8 @@ def test_cookiecutter(session: Session, replay_file_path: str) -> None:
     session.run("pre-commit", "run", "--all-files", external=True)
 
 
-@session(name="version-bump")
-def version_bump(session: Session) -> None:
+@nox.session(name="version-bump")
+def version_bump(session: nox.Session) -> None:
     """Run commitizen."""
     session.install(
         "commitizen",
@@ -295,4 +284,7 @@ def api_changes(session: nox.Session) -> None:
     if session.posargs:
         args.append(f"-a={session.posargs[0]}")
 
+    if "GITHUB_ACTIONS" in os.environ:
+        args.append("-f=github")
+
     session.run(*args, external=True)
diff --git a/poetry.lock b/poetry.lock
index 3d95d2389..fd0d25df8 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,25 +1,25 @@
-# This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.4 and should not be changed by hand.
 
 [[package]]
 name = "aiobotocore"
-version = "2.15.1"
+version = "2.15.2"
 description = "Async client for aws services using botocore and aiohttp"
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "aiobotocore-2.15.1-py3-none-any.whl", hash = "sha256:0f738cde74108553b753b24655094289a3c7ea0f0f179ed1c0f8cea488999a35"},
-    {file = "aiobotocore-2.15.1.tar.gz", hash = "sha256:1f9f16eec2a3da32df162b5db12da779ec6d6c6311715c936cad511f436efa74"},
+    {file = "aiobotocore-2.15.2-py3-none-any.whl", hash = "sha256:d4d3128b4b558e2b4c369bfa963b022d7e87303adb82eec623cec8aa77ae578a"},
+    {file = "aiobotocore-2.15.2.tar.gz", hash = "sha256:9ac1cfcaccccc80602968174aa032bf978abe36bd4e55e6781d6500909af1375"},
 ]
 
 [package.dependencies]
 aiohttp = ">=3.9.2,<4.0.0"
 aioitertools = ">=0.5.1,<1.0.0"
-botocore = ">=1.35.16,<1.35.24"
+botocore = ">=1.35.16,<1.35.37"
 wrapt = ">=1.10.10,<2.0.0"
 
 [package.extras]
-awscli = ["awscli (>=1.34.16,<1.34.24)"]
-boto3 = ["boto3 (>=1.35.16,<1.35.24)"]
+awscli = ["awscli (>=1.34.16,<1.35.3)"]
+boto3 = ["boto3 (>=1.35.16,<1.35.37)"]
 
 [[package]]
 name = "aiohappyeyeballs"
@@ -34,102 +34,102 @@ files = [
 
 [[package]]
 name = "aiohttp"
-version = "3.10.8"
+version = "3.10.10"
 description = "Async http client/server framework (asyncio)"
 optional = true
 python-versions = ">=3.8"
 files = [
-    {file = "aiohttp-3.10.8-cp310-cp310-macosx_10_9_universal2.whl", hash = "sha256:a1ba7bc139592339ddeb62c06486d0fa0f4ca61216e14137a40d626c81faf10c"},
-    {file = "aiohttp-3.10.8-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:85e4d7bd05d18e4b348441e7584c681eff646e3bf38f68b2626807f3add21aa2"},
-    {file = "aiohttp-3.10.8-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:69de056022e7abf69cb9fec795515973cc3eeaff51e3ea8d72a77aa933a91c52"},
-    {file = "aiohttp-3.10.8-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:ee3587506898d4a404b33bd19689286ccf226c3d44d7a73670c8498cd688e42c"},
-    {file = "aiohttp-3.10.8-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:fe285a697c851734285369614443451462ce78aac2b77db23567507484b1dc6f"},
-    {file = "aiohttp-3.10.8-cp310-cp310-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:10c7932337285a6bfa3a5fe1fd4da90b66ebfd9d0cbd1544402e1202eb9a8c3e"},
-    {file = "aiohttp-3.10.8-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:cd9716ef0224fe0d0336997eb242f40619f9f8c5c57e66b525a1ebf9f1d8cebe"},
-    {file = "aiohttp-3.10.8-cp310-cp310-manylinux_2_5_i686.manylinux1_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:ceacea31f8a55cdba02bc72c93eb2e1b77160e91f8abd605969c168502fd71eb"},
-    {file = "aiohttp-3.10.8-cp310-cp310-musllinux_1_2_aarch64.whl", hash = "sha256:9721554bfa9e15f6e462da304374c2f1baede3cb06008c36c47fa37ea32f1dc4"},
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 ]
 
 [package.dependencies]
@@ -372,17 +372,17 @@ lxml = ["lxml"]
 
 [[package]]
 name = "boto3"
-version = "1.35.23"
+version = "1.35.36"
 description = "The AWS SDK for Python"
 optional = false
 python-versions = ">=3.8"
 files = [
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+    {file = "boto3-1.35.36.tar.gz", hash = "sha256:586524b623e4fbbebe28b604c6205eb12f263cc4746bccb011562d07e217a4cb"},
 ]
 
 [package.dependencies]
-botocore = ">=1.35.23,<1.36.0"
+botocore = ">=1.35.36,<1.36.0"
 jmespath = ">=0.7.1,<2.0.0"
 s3transfer = ">=0.10.0,<0.11.0"
 
@@ -391,13 +391,13 @@ crt = ["botocore[crt] (>=1.21.0,<2.0a0)"]
 
 [[package]]
 name = "botocore"
-version = "1.35.23"
+version = "1.35.36"
 description = "Low-level, data-driven core of boto 3."
 optional = false
 python-versions = ">=3.8"
 files = [
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 ]
 
 [package.dependencies]
@@ -409,7 +409,7 @@ urllib3 = [
 ]
 
 [package.extras]
-crt = ["awscrt (==0.21.5)"]
+crt = ["awscrt (==0.22.0)"]
 
 [[package]]
 name = "cattrs"
@@ -529,101 +529,116 @@ pycparser = "*"
 
 [[package]]
 name = "charset-normalizer"
-version = "3.3.2"
+version = "3.4.0"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
 optional = false
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 [package.dependencies]
@@ -740,38 +745,38 @@ toml = ["tomli"]
 
 [[package]]
 name = "cryptography"
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 description = "cryptography is a package which provides cryptographic recipes and primitives to Python developers."
 optional = false
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 [package.dependencies]
@@ -784,7 +789,7 @@ nox = ["nox"]
 pep8test = ["check-sdist", "click", "mypy", "ruff"]
 sdist = ["build"]
 ssh = ["bcrypt (>=3.1.5)"]
-test = ["certifi", "cryptography-vectors (==43.0.1)", "pretend", "pytest (>=6.2.0)", "pytest-benchmark", "pytest-cov", "pytest-xdist"]
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 test-randomorder = ["pytest-randomly"]
 
 [[package]]
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 optional = false
 python-versions = "<4,>=3.8"
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 [package.dependencies]
@@ -917,13 +922,13 @@ test = ["pytest (>=6)"]
 
 [[package]]
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-version = "30.1.0"
+version = "30.8.2"
 description = "Faker is a Python package that generates fake data for you."
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 python-versions = ">=3.8"
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 [[package]]
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 [[package]]
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+version = "2024.10.0"
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+version = "1.7.0"
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 python-versions = "*"
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 [package.dependencies]
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 description = "Python port of markdown-it. Markdown parsing, done right!"
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 [[package]]
@@ -1522,7 +1539,7 @@ testing = ["coverage", "pytest", "pytest-cov", "pytest-regressions"]
 name = "mdurl"
 version = "0.1.2"
 description = "Markdown URL utilities"
-optional = true
+optional = false
 python-versions = ">=3.7"
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@@ -1531,18 +1548,18 @@ files = [
 
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 description = ""
 optional = false
 python-versions = ">=3.8"
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 cryptography = ">=3.3.1"
 Jinja2 = ">=2.10.1"
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 xmltodict = "*"
 
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 [package.dependencies]
@@ -1721,6 +1744,7 @@ typing-extensions = ">=4.6.0"
 
 [package.extras]
 dmypy = ["psutil (>=4.0)"]
+faster-cache = ["orjson"]
 install-types = ["pip"]
 mypyc = ["setuptools (>=50)"]
 reports = ["lxml"]
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-[package.dependencies]
-numpy = ">=1.16.6"
-
 [package.extras]
 test = ["cffi", "hypothesis", "pandas", "pytest", "pytz"]
 
@@ -2077,7 +2165,7 @@ files = [
 name = "pygments"
 version = "2.18.0"
 description = "Pygments is a syntax highlighting package written in Python."
-optional = true
+optional = false
 python-versions = ">=3.8"
 files = [
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@@ -2154,44 +2242,47 @@ dev = ["argcomplete", "attrs (>=19.2)", "hypothesis (>=3.56)", "mock", "pygments
 
 [[package]]
 name = "pytest-benchmark"
-version = "4.0.0"
+version = "5.1.0"
 description = "A ``pytest`` fixture for benchmarking code. It will group the tests into rounds that are calibrated to the chosen timer."
 optional = false
-python-versions = ">=3.7"
+python-versions = ">=3.9"
 files = [
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 ]
 
 [package.dependencies]
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-pytest = ">=3.8"
+pytest = ">=8.1"
 
 [package.extras]
 aspect = ["aspectlib"]
 elasticsearch = ["elasticsearch"]
-histogram = ["pygal", "pygaljs"]
+histogram = ["pygal", "pygaljs", "setuptools"]
 
 [[package]]
 name = "pytest-codspeed"
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+version = "3.0.0"
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+cffi = ">=1.17.1"
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+importlib-metadata = {version = ">=8.5.0", markers = "python_version < \"3.10\""}
 pytest = ">=3.8"
+rich = ">=13.8.1"
 setuptools = {version = "*", markers = "python_full_version >= \"3.12.0\""}
 
 [package.extras]
-compat = ["pytest-benchmark (>=4.0.0,<4.1.0)", "pytest-xdist (>=2.0.0,<2.1.0)"]
-lint = ["mypy (>=1.3.0,<1.4.0)", "ruff (>=0.3.3,<0.4.0)"]
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 test = ["pytest (>=7.0,<8.0)", "pytest-cov (>=4.0.0,<4.1.0)"]
 
 [[package]]
@@ -2440,133 +2531,139 @@ files = [
 [package.dependencies]
 six = "*"
 
+[[package]]
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+version = "13.9.4"
+description = "Render rich text, tables, progress bars, syntax highlighting, markdown and more to the terminal"
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+
+[package.extras]
+jupyter = ["ipywidgets (>=7.5.1,<9)"]
+
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-fsspec = "==2024.9.0.*"
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 [package.extras]
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 [[package]]
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 [[package]]
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 [package.dependencies]
@@ -3050,7 +3155,7 @@ aioodbc = ["aioodbc", "greenlet (!=0.4.17)"]
 aiosqlite = ["aiosqlite", "greenlet (!=0.4.17)", "typing_extensions (!=3.10.0.1)"]
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 mssql = ["pyodbc"]
 mssql-pymssql = ["pymssql"]
 mssql-pyodbc = ["pyodbc"]
@@ -3071,78 +3176,67 @@ sqlcipher = ["sqlcipher3_binary"]
 
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 [package.dependencies]
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+zstd = ["zstandard (>=0.18.0)"]
+
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+    {file = "yarl-1.17.1-py3-none-any.whl", hash = "sha256:f1790a4b1e8e8e028c391175433b9c8122c39b46e1663228158e61e6f915bf06"},
+    {file = "yarl-1.17.1.tar.gz", hash = "sha256:067a63fcfda82da6b198fa73079b1ca40b7c9b7994995b6ee38acda728b64d47"},
 ]
 
 [package.dependencies]
 idna = ">=2.0"
 multidict = ">=4.0"
+propcache = ">=0.2.0"
 
 [[package]]
 name = "zipp"
-version = "3.20.2"
+version = "3.21.0"
 description = "Backport of pathlib-compatible object wrapper for zip files"
 optional = false
-python-versions = ">=3.8"
+python-versions = ">=3.9"
 files = [
-    {file = "zipp-3.20.2-py3-none-any.whl", hash = "sha256:a817ac80d6cf4b23bf7f2828b7cabf326f15a001bea8b1f9b49631780ba28350"},
-    {file = "zipp-3.20.2.tar.gz", hash = "sha256:bc9eb26f4506fda01b81bcde0ca78103b6e62f991b381fec825435c836edbc29"},
+    {file = "zipp-3.21.0-py3-none-any.whl", hash = "sha256:ac1bbe05fd2991f160ebce24ffbac5f6d11d83dc90891255885223d42b3cd931"},
+    {file = "zipp-3.21.0.tar.gz", hash = "sha256:2c9958f6430a2040341a52eb608ed6dd93ef4392e02ffe219417c1b28b5dd1f4"},
 ]
 
 [package.extras]
@@ -3534,12 +3650,12 @@ type = ["pytest-mypy"]
 docs = ["furo", "myst-parser", "pytest", "sphinx", "sphinx-copybutton", "sphinx-inline-tabs", "sphinx-notfound-page", "sphinx-reredirects"]
 faker = ["faker"]
 jwt = ["PyJWT", "cryptography"]
-parquet = ["numpy", "numpy", "numpy", "pyarrow"]
+parquet = ["numpy", "numpy", "pyarrow"]
 s3 = ["fs-s3fs", "s3fs"]
 ssh = ["paramiko"]
 testing = ["pytest"]
 
 [metadata]
 lock-version = "2.0"
-python-versions = ">=3.8"
-content-hash = "54b2b2caf41a6f8c058f4e40b00fb33031c86cdea138bce71d457a94a03f164b"
+python-versions = ">=3.9"
+content-hash = "3e5dc4b61042912409c6e4866ea70b7fe12581eea4bf73468f1e6d494332d5f8"
diff --git a/pyproject.toml b/pyproject.toml
index 83410902f..589fb6336 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -19,11 +19,11 @@ classifiers = [
     "Intended Audience :: Developers",
     "License :: OSI Approved :: Apache Software License",
     "Operating System :: OS Independent",
-    "Programming Language :: Python :: 3.8",
     "Programming Language :: Python :: 3.9",
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
     "Programming Language :: Python :: Implementation :: CPython",
     "Topic :: Software Development :: Libraries :: Application Frameworks",
     "Typing :: Typed",
@@ -38,7 +38,7 @@ license = "Apache-2.0"
 "Youtube" = "https://www.youtube.com/meltano"
 
 [tool.poetry.dependencies]
-python = ">=3.8"
+python = ">=3.9"
 backoff = { version = ">=2.0.0", python = "<4" }
 backports-datetime-fromisoformat = { version = ">=2.0.1", python = "<3.11" }
 click = "~=8.0"
@@ -58,22 +58,20 @@ requests = ">=2.25.1"
 # TODO: remove this constraint once we get rid of the `fs` dependency
 # newer setuptools versions are incompatible with some dependencies (fs)
 setuptools = "<=70.3.0"
-simpleeval = ">=0.9.13"
+simpleeval = ">=0.9.13,!=1.0.1"
 simplejson = ">=3.17.6"
 sqlalchemy = ">=1.4,<3.0"
 typing-extensions = ">=4.5.0"
-# urllib3 2.0 is not compatible with botocore
-urllib3 = ">=1.26,<2"
 
 # Sphinx dependencies installed as optional 'docs' extras
 # https://github.com/readthedocs/readthedocs.org/issues/4912#issuecomment-664002569
-furo = {version = ">=2024.5.6", python = ">=3.9", optional = true}
-myst-parser = {version = ">=3", python = ">=3.9", optional = true}
-sphinx = {version = ">=7", python = ">=3.9", optional = true}
-sphinx-copybutton = {version = ">=0.5.2", python = ">=3.9", optional = true}
-sphinx-inline-tabs = {version = ">=2023.4.21", python = ">=3.9", optional = true}
-sphinx-notfound-page = {version = ">=1.0.0", python = ">=3.9", optional = true}
-sphinx-reredirects = {version = ">=0.1.5", python = ">=3.9", optional = true}
+furo = {version = ">=2024.5.6", optional = true}
+myst-parser = {version = ">=3", optional = true}
+sphinx = {version = ">=7", optional = true}
+sphinx-copybutton = {version = ">=0.5.2", optional = true}
+sphinx-inline-tabs = {version = ">=2023.4.21", optional = true}
+sphinx-notfound-page = {version = ">=1.0.0", optional = true}
+sphinx-reredirects = {version = ">=0.1.5", optional = true}
 
 # File storage dependencies installed as optional 'filesystem' extras
 fs-s3fs = {version = ">=1.1.1", optional = true}
@@ -85,7 +83,6 @@ s3fs = { version = ">=2024.9.0", optional = true }
 # the version of Numpy that is compatible with the earliest Python version supported
 # by this project, but that may not be compatible with the latest Python version.
 numpy = [
-    { version = ">=1.22,<1.25", python = "==3.8", optional = true },
     { version = ">=1.22,<2.1", python = "==3.9", optional = true },
     { version = ">=1.22", python = ">=3.10", optional = true },
 ]
@@ -160,7 +157,6 @@ pytest-codspeed = ">=2.2.0"
 [tool.pytest.ini_options]
 addopts = [
     "--durations=10",
-    "--ignore=singer_sdk/helpers/_simpleeval.py",
     "-m",
     "not external",
     "-ra",
@@ -173,19 +169,10 @@ filterwarnings = [
     "ignore:No records were available to test:UserWarning",
     # https://github.com/meltano/sdk/issues/1354
     "ignore:The function singer_sdk.testing.get_standard_tap_tests is deprecated:DeprecationWarning",
-    # https://docs.python.org/3.12/whatsnew/3.12.html#deprecated
-    # https://github.com/danthedeckie/simpleeval/blob/master/simpleeval.py
-    "ignore:ast.NameConstant is deprecated:DeprecationWarning:simpleeval",
-    # https://docs.python.org/3.12/whatsnew/3.12.html#deprecated
-    # https://github.com/danthedeckie/simpleeval/blob/master/simpleeval.py
-    "ignore:ast.Num is deprecated:DeprecationWarning:simpleeval",
-    # https://github.com/joblib/joblib/pull/1518
-    "ignore:ast.Num is deprecated:DeprecationWarning:joblib._utils",
-    # https://docs.python.org/3.12/whatsnew/3.12.html#deprecated
-    # https://github.com/danthedeckie/simpleeval/blob/master/simpleeval.py
-    "ignore:ast.Str is deprecated:DeprecationWarning:simpleeval",
-    # https://github.com/joblib/joblib/pull/1518
-    "ignore:Attribute n is deprecated:DeprecationWarning:joblib._utils",
+    # https://github.com/meltano/sdk/issues/2744
+    "default::singer_sdk.helpers._compat.SingerSDKDeprecationWarning",
+    # TODO: Address this SQLite warning in Python 3.13+
+    "ignore::ResourceWarning",
 ]
 log_cli_level = "INFO"
 markers = [
@@ -200,7 +187,7 @@ xfail_strict = false
 
 [tool.commitizen]
 name = "cz_version_bump"
-version = "0.41.0"
+version = "0.42.1"
 changelog_merge_prerelease = true
 prerelease_offset = 1
 tag_format = "v$major.$minor.$patch$prerelease"
@@ -322,10 +309,9 @@ parquet = "singer_sdk.contrib.batch_encoder_parquet:ParquetBatcher"
 [tool.ruff]
 extend-exclude = [
     "cookiecutter/*",
-    "*simpleeval*",
 ]
 line-length = 88
-target-version = "py38"
+target-version = "py39"
 
 [tool.ruff.format]
 docstring-code-format = true
diff --git a/samples/aapl/aapl.py b/samples/aapl/aapl.py
index 1e7c78b86..d6605d4ea 100644
--- a/samples/aapl/aapl.py
+++ b/samples/aapl/aapl.py
@@ -2,17 +2,12 @@
 
 from __future__ import annotations
 
+import importlib.resources
 import json
-import sys
 
 from singer_sdk import Stream, Tap
 
-if sys.version_info < (3, 9):
-    import importlib_resources
-else:
-    import importlib.resources as importlib_resources
-
-PROJECT_DIR = importlib_resources.files("samples.aapl")
+PROJECT_DIR = importlib.resources.files("samples.aapl")
 
 
 class AAPL(Stream):
diff --git a/samples/sample_mapper/mapper.py b/samples/sample_mapper/mapper.py
index 0a7899d37..67052bbe4 100644
--- a/samples/sample_mapper/mapper.py
+++ b/samples/sample_mapper/mapper.py
@@ -40,6 +40,7 @@ class StreamTransform(InlineMapper):
                 ),
             ),
             required=True,
+            title="Stream Maps",
             description="Stream maps",
         ),
     ).to_dict()
diff --git a/samples/sample_tap_bigquery/__init__.py b/samples/sample_tap_bigquery/__init__.py
index 098be2525..ad0d3c3cb 100644
--- a/samples/sample_tap_bigquery/__init__.py
+++ b/samples/sample_tap_bigquery/__init__.py
@@ -52,6 +52,7 @@ class TapBigQuery(SQLTap):
             "project_id",
             th.StringType,
             required=True,
+            title="Project ID",
             description="GCP Project",
         ),
     ).to_dict()
diff --git a/samples/sample_tap_countries/countries_streams.py b/samples/sample_tap_countries/countries_streams.py
index 2b3ebfa90..d0106ff06 100644
--- a/samples/sample_tap_countries/countries_streams.py
+++ b/samples/sample_tap_countries/countries_streams.py
@@ -9,7 +9,7 @@
 from __future__ import annotations
 
 import abc
-import sys
+import importlib.resources
 import typing as t
 
 from requests_cache.session import CachedSession
@@ -17,13 +17,7 @@
 from singer_sdk import typing as th
 from singer_sdk.streams.graphql import GraphQLStream
 
-if sys.version_info < (3, 9):
-    import importlib_resources
-else:
-    from importlib import resources as importlib_resources
-
-
-SCHEMAS_DIR = importlib_resources.files(__package__) / "schemas"
+SCHEMAS_DIR = importlib.resources.files(__package__) / "schemas"
 
 
 class CountriesAPIStream(GraphQLStream, metaclass=abc.ABCMeta):
diff --git a/samples/sample_tap_csv/sample_tap_csv.py b/samples/sample_tap_csv/sample_tap_csv.py
index 71c8b3d1d..ed469c9ee 100644
--- a/samples/sample_tap_csv/sample_tap_csv.py
+++ b/samples/sample_tap_csv/sample_tap_csv.py
@@ -19,30 +19,35 @@ class SampleTapCSV(FolderTap):
             "delimiter",
             th.StringType,
             default=",",
+            title="Delimiter",
             description="Field delimiter character.",
         ),
         th.Property(
             "quotechar",
             th.StringType,
             default='"',
+            title="Quote Character",
             description="Quote character.",
         ),
         th.Property(
             "escapechar",
             th.StringType,
             default=None,
+            title="Escape Character",
             description="Escape character.",
         ),
         th.Property(
             "doublequote",
             th.BooleanType,
             default=True,
+            title="Double Quote",
             description="Whether quotechar inside a field should be doubled.",
         ),
         th.Property(
             "lineterminator",
             th.StringType,
             default="\r\n",
+            title="Line Terminator",
             description="Line terminator character.",
         ),
     ).to_dict()
diff --git a/samples/sample_tap_dummy_json/README.md b/samples/sample_tap_dummy_json/README.md
index e154663d9..92ff0cbe4 100644
--- a/samples/sample_tap_dummy_json/README.md
+++ b/samples/sample_tap_dummy_json/README.md
@@ -122,7 +122,7 @@ Now you can test and orchestrate using Meltano:
 # Test invocation:
 meltano invoke tap-dummyjson --version
 # OR run a test `elt` pipeline:
-meltano elt tap-dummyjson target-jsonl
+meltano run tap-dummyjson target-jsonl
 ```
 
 ### SDK Dev Guide
diff --git a/samples/sample_tap_dummy_json/pyproject.toml b/samples/sample_tap_dummy_json/pyproject.toml
index c72347748..4542c6448 100644
--- a/samples/sample_tap_dummy_json/pyproject.toml
+++ b/samples/sample_tap_dummy_json/pyproject.toml
@@ -15,6 +15,7 @@ classifiers = [
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
+    "Programming Language :: Python :: 3.13",
 ]
 license = "Apache-2.0"
 
diff --git a/samples/sample_tap_dummy_json/ruff.toml b/samples/sample_tap_dummy_json/ruff.toml
index dd2f13459..c6af4cfef 100644
--- a/samples/sample_tap_dummy_json/ruff.toml
+++ b/samples/sample_tap_dummy_json/ruff.toml
@@ -1,5 +1,5 @@
 src = ["tap_dummyjson"]
-target-version = "py38"
+target-version = "py39"
 
 [lint]
 ignore = [
diff --git a/samples/sample_tap_dummy_json/tap_dummyjson/tap.py b/samples/sample_tap_dummy_json/tap_dummyjson/tap.py
index b352d0172..40b1f0169 100644
--- a/samples/sample_tap_dummy_json/tap_dummyjson/tap.py
+++ b/samples/sample_tap_dummy_json/tap_dummyjson/tap.py
@@ -14,6 +14,7 @@ class TapDummyJSON(Tap):
             "username",
             th.StringType,
             required=True,
+            title="DummyJSON Username",
             description="Username for the API service",
         ),
         th.Property(
@@ -21,16 +22,19 @@ class TapDummyJSON(Tap):
             th.StringType,
             required=True,
             secret=True,  # Flag config as protected.
+            title="DummyJSON Password",
             description="Password for the API service",
         ),
         th.Property(
             "start_date",
             th.DateTimeType,
+            title="Start Date",
             description="The earliest record date to sync",
         ),
         th.Property(
             "api_url",
             th.StringType,
+            title="API URL",
             default="https://dummyjson.com",
             description="The base url for the API service",
         ),
diff --git a/samples/sample_tap_dummy_json/tox.ini b/samples/sample_tap_dummy_json/tox.ini
index 6be1c116a..8b89a4ef1 100644
--- a/samples/sample_tap_dummy_json/tox.ini
+++ b/samples/sample_tap_dummy_json/tox.ini
@@ -1,7 +1,7 @@
 # This file can be used to customize tox tests as well as other test frameworks like flake8 and mypy
 
 [tox]
-envlist = py{38,39,310,311,312}
+envlist = py3{9,10,11,12,13}
 isolated_build = true
 
 [testenv]
@@ -13,7 +13,7 @@ commands =
 [testenv:pytest]
 # Run the python tests.
 # To execute, run `tox -e pytest`
-envlist = py{38,39,310,311,312}
+envlist = py3{8,9,10,11,12,313}
 commands =
     poetry install -v
     poetry run pytest
diff --git a/samples/sample_tap_gitlab/gitlab_graphql_streams.py b/samples/sample_tap_gitlab/gitlab_graphql_streams.py
index 540b77466..f675e29f0 100644
--- a/samples/sample_tap_gitlab/gitlab_graphql_streams.py
+++ b/samples/sample_tap_gitlab/gitlab_graphql_streams.py
@@ -6,19 +6,13 @@
 
 from __future__ import annotations
 
-import sys
+import importlib.resources
 
 from singer_sdk.streams import GraphQLStream
 
-if sys.version_info < (3, 9):
-    import importlib_resources
-else:
-    from importlib import resources as importlib_resources
-
-
 SITE_URL = "https://gitlab.com/graphql"
 
-SCHEMAS_DIR = importlib_resources.files(__package__) / "schemas"
+SCHEMAS_DIR = importlib.resources.files(__package__) / "schemas"
 
 
 class GitlabGraphQLStream(GraphQLStream):
diff --git a/samples/sample_tap_gitlab/gitlab_rest_streams.py b/samples/sample_tap_gitlab/gitlab_rest_streams.py
index f81e4df59..5ed59f666 100644
--- a/samples/sample_tap_gitlab/gitlab_rest_streams.py
+++ b/samples/sample_tap_gitlab/gitlab_rest_streams.py
@@ -2,7 +2,7 @@
 
 from __future__ import annotations
 
-import sys
+import importlib.resources
 import typing as t
 
 from singer_sdk.authenticators import SimpleAuthenticator
@@ -19,13 +19,7 @@
     StringType,
 )
 
-if sys.version_info < (3, 9):
-    import importlib_resources
-else:
-    from importlib import resources as importlib_resources
-
-
-SCHEMAS_DIR = importlib_resources.files(__package__) / "schemas"
+SCHEMAS_DIR = importlib.resources.files(__package__) / "schemas"
 
 DEFAULT_URL_BASE = "https://gitlab.com/api/v4"
 
diff --git a/samples/sample_tap_gitlab/gitlab_tap.py b/samples/sample_tap_gitlab/gitlab_tap.py
index 952e406ae..56164fc2c 100644
--- a/samples/sample_tap_gitlab/gitlab_tap.py
+++ b/samples/sample_tap_gitlab/gitlab_tap.py
@@ -34,10 +34,14 @@ class SampleTapGitlab(Tap):
 
     name: str = "sample-tap-gitlab"
     config_jsonschema = PropertiesList(
-        Property("auth_token", StringType, required=True, secret=True),
-        Property("project_ids", ArrayType(StringType), required=True),
-        Property("group_ids", ArrayType(StringType), required=True),
-        Property("start_date", DateTimeType, required=True),
+        Property(
+            "auth_token", StringType, required=True, secret=True, title="Auth Token"
+        ),
+        Property(
+            "project_ids", ArrayType(StringType), required=True, title="Project IDs"
+        ),
+        Property("group_ids", ArrayType(StringType), required=True, title="Group IDs"),
+        Property("start_date", DateTimeType, required=True, title="Start Date"),
     ).to_dict()
 
     def discover_streams(self) -> list[Stream]:
diff --git a/samples/sample_tap_sqlite/__init__.py b/samples/sample_tap_sqlite/__init__.py
index 51add7136..2215cbfe7 100644
--- a/samples/sample_tap_sqlite/__init__.py
+++ b/samples/sample_tap_sqlite/__init__.py
@@ -48,6 +48,7 @@ class SQLiteTap(SQLTap):
         th.Property(
             DB_PATH_CONFIG,
             th.StringType,
+            title="Database Path",
             description="The path to your SQLite database file(s).",
             required=True,
             examples=["./path/to/my.db", "/absolute/path/to/my.db"],
diff --git a/samples/sample_target_csv/csv_target.py b/samples/sample_target_csv/csv_target.py
index d52b76f48..6e800970c 100644
--- a/samples/sample_target_csv/csv_target.py
+++ b/samples/sample_target_csv/csv_target.py
@@ -12,7 +12,9 @@ class SampleTargetCSV(Target):
 
     name = "target-csv"
     config_jsonschema = th.PropertiesList(
-        th.Property("target_folder", th.StringType, required=True),
-        th.Property("file_naming_scheme", th.StringType),
+        th.Property(
+            "target_folder", th.StringType, required=True, title="Target Folder"
+        ),
+        th.Property("file_naming_scheme", th.StringType, title="File Naming Scheme"),
     ).to_dict()
     default_sink_class = SampleCSVTargetSink
diff --git a/samples/sample_target_parquet/parquet_target.py b/samples/sample_target_parquet/parquet_target.py
index d8c8f7a74..f0cda3d4d 100644
--- a/samples/sample_target_parquet/parquet_target.py
+++ b/samples/sample_target_parquet/parquet_target.py
@@ -12,8 +12,8 @@ class SampleTargetParquet(Target):
 
     name = "sample-target-parquet"
     config_jsonschema = th.PropertiesList(
-        th.Property("filepath", th.StringType),
-        th.Property("file_naming_scheme", th.StringType),
+        th.Property("filepath", th.StringType, title="Output File Path"),
+        th.Property("file_naming_scheme", th.StringType, title="File Naming Scheme"),
     ).to_dict()
     default_sink_class = SampleParquetTargetSink
 
diff --git a/samples/sample_target_parquet/parquet_target_sink.py b/samples/sample_target_parquet/parquet_target_sink.py
index e98dca2b1..fbdd13cd1 100644
--- a/samples/sample_target_parquet/parquet_target_sink.py
+++ b/samples/sample_target_parquet/parquet_target_sink.py
@@ -4,11 +4,14 @@
 
 import typing as t
 
-import pyarrow as pa
-import pyarrow.parquet as pq
-
 from singer_sdk.sinks import BatchSink
 
+try:
+    import pyarrow as pa
+    import pyarrow.parquet as pq
+except ImportError:
+    pass
+
 
 def json_schema_to_arrow(schema: dict[str, t.Any]) -> pa.Schema:
     """Convert a JSON Schema to an Arrow schema.
diff --git a/samples/sample_target_sqlite/__init__.py b/samples/sample_target_sqlite/__init__.py
index d296c5fb0..0e1062642 100644
--- a/samples/sample_target_sqlite/__init__.py
+++ b/samples/sample_target_sqlite/__init__.py
@@ -51,6 +51,7 @@ class SQLiteTarget(SQLTarget):
         th.Property(
             DB_PATH_CONFIG,
             th.StringType,
+            title="Database Path",
             description="The path to your SQLite database file(s).",
             required=True,
         ),
diff --git a/singer_sdk/_singerlib/catalog.py b/singer_sdk/_singerlib/catalog.py
index c39d46a1b..986272e3c 100644
--- a/singer_sdk/_singerlib/catalog.py
+++ b/singer_sdk/_singerlib/catalog.py
@@ -11,12 +11,12 @@
     from typing_extensions import TypeAlias
 
 
-Breadcrumb = t.Tuple[str, ...]
+Breadcrumb = tuple[str, ...]
 
 logger = logging.getLogger(__name__)
 
 
-class SelectionMask(t.Dict[Breadcrumb, bool]):
+class SelectionMask(dict[Breadcrumb, bool]):
     """Boolean mask for property selection in schemas and records."""
 
     def __missing__(self, breadcrumb: Breadcrumb) -> bool:
@@ -95,7 +95,7 @@ class StreamMetadata(Metadata):
 AnyMetadata: TypeAlias = t.Union[Metadata, StreamMetadata]
 
 
-class MetadataMapping(t.Dict[Breadcrumb, AnyMetadata]):
+class MetadataMapping(dict[Breadcrumb, AnyMetadata]):
     """Stream metadata mapping."""
 
     @classmethod
@@ -352,7 +352,7 @@ def to_dict(self) -> dict[str, t.Any]:  # noqa: C901
         return result
 
 
-class Catalog(t.Dict[str, CatalogEntry]):
+class Catalog(dict[str, CatalogEntry]):
     """Singer catalog mapping of stream entries."""
 
     @classmethod
diff --git a/singer_sdk/_singerlib/encoding/_base.py b/singer_sdk/_singerlib/encoding/_base.py
index 62793776b..404c6ed6c 100644
--- a/singer_sdk/_singerlib/encoding/_base.py
+++ b/singer_sdk/_singerlib/encoding/_base.py
@@ -38,6 +38,10 @@ class SingerMessageType(str, enum.Enum):
 class GenericSingerReader(t.Generic[T], metaclass=abc.ABCMeta):
     """Interface for all plugins reading Singer messages as strings or bytes."""
 
+    def __init__(self) -> None:
+        super().__init__()
+        self._current_message: T | None = None
+
     @t.final
     def listen(self, file_input: t.IO[T] | None = None) -> None:
         """Read from input until all messages are processed.
@@ -45,7 +49,14 @@ def listen(self, file_input: t.IO[T] | None = None) -> None:
         Args:
             file_input: Readable stream of messages. Defaults to standard in.
         """
-        self._process_lines(file_input or self.default_input)
+        try:
+            self._process_lines(file_input or self.default_input)
+        except Exception:
+            logger.debug(
+                "Failed while processing Singer message: %s",
+                self._current_message,
+            )
+            raise
         self._process_endofpipe()
 
     def _process_lines(self, file_input: t.IO[T]) -> t.Counter[str]:
@@ -59,6 +70,8 @@ def _process_lines(self, file_input: t.IO[T]) -> t.Counter[str]:
         """
         stats: dict[str, int] = defaultdict(int)
         for line in file_input:
+            self._current_message = line
+
             line_dict = self.deserialize_json(line)
             self._assert_line_requires(line_dict, requires={"type"})
 
diff --git a/singer_sdk/about.py b/singer_sdk/about.py
index ab3062295..ac1e76fa8 100644
--- a/singer_sdk/about.py
+++ b/singer_sdk/about.py
@@ -23,8 +23,8 @@
 ]
 
 # Keep these in sync with the supported Python versions in pyproject.toml
-_PY_MIN_VERSION = 8
-_PY_MAX_VERSION = 12
+_PY_MIN_VERSION = 9
+_PY_MAX_VERSION = 13
 
 
 def _get_min_version(specifiers: SpecifierSet) -> int:
diff --git a/singer_sdk/authenticators.py b/singer_sdk/authenticators.py
index 3a7fd8833..916669ef7 100644
--- a/singer_sdk/authenticators.py
+++ b/singer_sdk/authenticators.py
@@ -22,7 +22,7 @@
 if t.TYPE_CHECKING:
     import logging
 
-    from singer_sdk.streams.rest import RESTStream
+    from singer_sdk.streams.rest import _HTTPStream
 
 
 def _add_parameters(initial_url: str, extra_parameters: dict) -> str:
@@ -91,7 +91,7 @@ class APIAuthenticatorBase:
         auth_params: URL query parameters for authentication.
     """
 
-    def __init__(self, stream: RESTStream) -> None:
+    def __init__(self, stream: _HTTPStream) -> None:
         """Init authenticator.
 
         Args:
@@ -156,7 +156,7 @@ class SimpleAuthenticator(APIAuthenticatorBase):
 
     def __init__(
         self,
-        stream: RESTStream,
+        stream: _HTTPStream,
         auth_headers: dict | None = None,
     ) -> None:
         """Create a new authenticator.
@@ -186,7 +186,7 @@ class APIKeyAuthenticator(APIAuthenticatorBase):
 
     def __init__(
         self,
-        stream: RESTStream,
+        stream: _HTTPStream,
         key: str,
         value: str,
         location: str = "header",
@@ -221,7 +221,7 @@ def __init__(
     @classmethod
     def create_for_stream(
         cls: type[APIKeyAuthenticator],
-        stream: RESTStream,
+        stream: _HTTPStream,
         key: str,
         value: str,
         location: str,
@@ -249,7 +249,7 @@ class BearerTokenAuthenticator(APIAuthenticatorBase):
     'Bearer '. The token will be merged with HTTP headers on the stream.
     """
 
-    def __init__(self, stream: RESTStream, token: str) -> None:
+    def __init__(self, stream: _HTTPStream, token: str) -> None:
         """Create a new authenticator.
 
         Args:
@@ -266,7 +266,7 @@ def __init__(self, stream: RESTStream, token: str) -> None:
     @classmethod
     def create_for_stream(
         cls: type[BearerTokenAuthenticator],
-        stream: RESTStream,
+        stream: _HTTPStream,
         token: str,
     ) -> BearerTokenAuthenticator:
         """Create an Authenticator object specific to the Stream class.
@@ -299,7 +299,7 @@ class BasicAuthenticator(APIAuthenticatorBase):
 
     def __init__(
         self,
-        stream: RESTStream,
+        stream: _HTTPStream,
         username: str,
         password: str,
     ) -> None:
@@ -323,7 +323,7 @@ def __init__(
     @classmethod
     def create_for_stream(
         cls: type[BasicAuthenticator],
-        stream: RESTStream,
+        stream: _HTTPStream,
         username: str,
         password: str,
     ) -> BasicAuthenticator:
@@ -346,7 +346,7 @@ class OAuthAuthenticator(APIAuthenticatorBase):
 
     def __init__(
         self,
-        stream: RESTStream,
+        stream: _HTTPStream,
         auth_endpoint: str | None = None,
         oauth_scopes: str | None = None,
         default_expiration: int | None = None,
diff --git a/singer_sdk/configuration/_dict_config.py b/singer_sdk/configuration/_dict_config.py
index fd8217f01..af1d19f29 100644
--- a/singer_sdk/configuration/_dict_config.py
+++ b/singer_sdk/configuration/_dict_config.py
@@ -10,11 +10,21 @@
 from dotenv import find_dotenv
 from dotenv.main import DotEnv
 
-from singer_sdk.helpers._typing import is_string_array_type
-from singer_sdk.helpers._util import read_json_file
+from singer_sdk.helpers import _typing
+from singer_sdk.helpers._util import load_json, read_json_file
 
 logger = logging.getLogger(__name__)
 
+TRUTHY = ("true", "1", "yes", "on")
+
+
+def _parse_array(value: str) -> list[str]:
+    return load_json(value)  # type: ignore[return-value]
+
+
+def _legacy_parse_array_of_strings(value: str) -> list[str]:
+    return value.split(",")
+
 
 def parse_environment_config(
     config_schema: dict[str, t.Any],
@@ -29,9 +39,6 @@ def parse_environment_config(
         dotenv_path: Path to a .env file. If None, will try to find one in increasingly
             higher folders.
 
-    Raises:
-        ValueError: If an un-parsable setting is found.
-
     Returns:
         A configuration dictionary.
     """
@@ -43,7 +50,7 @@ def parse_environment_config(
     logger.debug("Loading configuration from %s", dotenv_path)
     DotEnv(dotenv_path).set_as_environment_variables()
 
-    for config_key in config_schema["properties"]:
+    for config_key, schema in config_schema.get("properties", {}).items():
         env_var_name = prefix + config_key.upper().replace("-", "_")
         if env_var_name in os.environ:
             env_var_value = os.environ[env_var_name]
@@ -52,15 +59,25 @@ def parse_environment_config(
                 config_key,
                 env_var_name,
             )
-            if is_string_array_type(config_schema["properties"][config_key]):
-                if env_var_value[0] == "[" and env_var_value[-1] == "]":
-                    msg = (
-                        "A bracketed list was detected in the environment variable "
-                        f"'{env_var_name}'. This syntax is no longer supported. Please "
-                        "remove the brackets and try again."
+            if _typing.is_integer_type(schema):
+                result[config_key] = int(env_var_value)
+            elif _typing.is_boolean_type(schema):
+                result[config_key] = env_var_value.lower() in TRUTHY
+            elif _typing.is_string_array_type(schema):
+                try:
+                    result[config_key] = _parse_array(env_var_value)
+                except Exception:  # noqa: BLE001
+                    # TODO(edgarrmondragon): Make this a deprecation warning.
+                    # https://github.com/meltano/sdk/issues/2724
+                    logger.warning(
+                        "Parsing array of the form 'x,y,z' is deprecated and will be "
+                        "removed in future versions.",
                     )
-                    raise ValueError(msg)
-                result[config_key] = env_var_value.split(",")
+                    result[config_key] = _legacy_parse_array_of_strings(env_var_value)
+            elif _typing.is_array_type(schema):
+                result[config_key] = _parse_array(env_var_value)
+            elif _typing.is_object_type(schema):
+                result[config_key] = load_json(env_var_value)
             else:
                 result[config_key] = env_var_value
     return result
diff --git a/singer_sdk/connectors/sql.py b/singer_sdk/connectors/sql.py
index 87eb1eb98..0368e8a5c 100644
--- a/singer_sdk/connectors/sql.py
+++ b/singer_sdk/connectors/sql.py
@@ -25,6 +25,11 @@
 else:
     from warnings import deprecated
 
+if sys.version_info < (3, 10):
+    from typing_extensions import TypeAlias
+else:
+    from typing import TypeAlias  # noqa: ICN003
+
 if t.TYPE_CHECKING:
     from sqlalchemy.engine import Engine
     from sqlalchemy.engine.reflection import Inspector
@@ -192,6 +197,227 @@ def boolean_to_jsonschema(self, column_type: sa.types.Boolean) -> dict:  # noqa:
         return th.BooleanType.type_dict  # type: ignore[no-any-return]
 
 
+JSONtoSQLHandler: TypeAlias = t.Union[
+    type[sa.types.TypeEngine],
+    t.Callable[[dict], sa.types.TypeEngine],
+]
+
+
+class JSONSchemaToSQL:
+    """A configurable mapper for converting JSON Schema types to SQLAlchemy types.
+
+    This class provides a mapping from JSON Schema types to SQLAlchemy types.
+
+    .. versionadded:: 0.42.0
+    """
+
+    def __init__(self) -> None:
+        """Initialize the mapper with default type mappings."""
+        # Default type mappings
+        self._type_mapping: dict[str, JSONtoSQLHandler] = {
+            "string": self._handle_string_type,
+            "integer": sa.types.INTEGER,
+            "number": sa.types.DECIMAL,
+            "boolean": sa.types.BOOLEAN,
+            "object": sa.types.VARCHAR,
+            "array": sa.types.VARCHAR,
+        }
+
+        # Format handlers for string types
+        self._format_handlers: dict[str, JSONtoSQLHandler] = {
+            # Default date-like formats
+            "date-time": sa.types.DATETIME,
+            "time": sa.types.TIME,
+            "date": sa.types.DATE,
+            # Common string formats with sensible defaults
+            "uuid": sa.types.UUID,
+            "email": lambda _: sa.types.VARCHAR(254),  # RFC 5321
+            "uri": lambda _: sa.types.VARCHAR(2083),  # Common browser limit
+            "hostname": lambda _: sa.types.VARCHAR(253),  # RFC 1035
+            "ipv4": lambda _: sa.types.VARCHAR(15),
+            "ipv6": lambda _: sa.types.VARCHAR(45),
+        }
+
+        self._fallback_type: type[sa.types.TypeEngine] = sa.types.VARCHAR
+
+    def _invoke_handler(  # noqa: PLR6301
+        self,
+        handler: JSONtoSQLHandler,
+        schema: dict,
+    ) -> sa.types.TypeEngine:
+        """Invoke a handler, handling both type classes and callables.
+
+        Args:
+            handler: The handler to invoke.
+            schema: The schema to pass to callable handlers.
+
+        Returns:
+            The resulting SQLAlchemy type.
+        """
+        if isinstance(handler, type):
+            return handler()  # type: ignore[no-any-return]
+        return handler(schema)
+
+    @property
+    def fallback_type(self) -> type[sa.types.TypeEngine]:
+        """Return the fallback type.
+
+        Returns:
+            The fallback type.
+        """
+        return self._fallback_type
+
+    @fallback_type.setter
+    def fallback_type(self, value: type[sa.types.TypeEngine]) -> None:
+        """Set the fallback type.
+
+        Args:
+            value: The new fallback type.
+        """
+        self._fallback_type = value
+
+    def register_type_handler(self, json_type: str, handler: JSONtoSQLHandler) -> None:
+        """Register a custom type handler.
+
+        Args:
+            json_type: The JSON Schema type to handle.
+            handler: Either a SQLAlchemy type class or a callable that takes a schema
+                    dict and returns a SQLAlchemy type instance.
+        """
+        self._type_mapping[json_type] = handler
+
+    def register_format_handler(
+        self,
+        format_name: str,
+        handler: JSONtoSQLHandler,
+    ) -> None:
+        """Register a custom format handler.
+
+        Args:
+            format_name: The format string (e.g., "date-time", "email", "custom-format").
+            handler: Either a SQLAlchemy type class or a callable that takes a schema
+                    dict and returns a SQLAlchemy type instance.
+        """  # noqa: E501
+        self._format_handlers[format_name] = handler
+
+    def handle_multiple_types(self, types: t.Sequence[str]) -> sa.types.TypeEngine:  # noqa: ARG002, PLR6301
+        """Handle multiple types by returning a VARCHAR.
+
+        Args:
+            types: The list of types to handle.
+
+        Returns:
+            A VARCHAR type.
+        """
+        return sa.types.VARCHAR()
+
+    def handle_raw_string(self, schema: dict) -> sa.types.TypeEngine:  # noqa: PLR6301
+        """Handle a string type generically.
+
+        Args:
+            schema: The JSON Schema object.
+
+        Returns:
+            Appropriate SQLAlchemy type.
+        """
+        max_length: int | None = schema.get("maxLength")
+        return sa.types.VARCHAR(max_length)
+
+    def _get_type_from_schema(self, schema: dict) -> sa.types.TypeEngine | None:
+        """Try to get a SQL type from a single schema object.
+
+        Args:
+            schema: The JSON Schema object.
+
+        Returns:
+            SQL type if one can be determined, None otherwise.
+        """
+        # Check if this is a string with format first
+        if schema.get("type") == "string" and "format" in schema:
+            format_type = self._handle_format(schema)
+            if format_type is not None:
+                return format_type
+
+        # Then check regular types
+        if schema_type := schema.get("type"):
+            if isinstance(schema_type, (list, tuple)):
+                # Filter out null type if present
+                non_null_types = [t for t in schema_type if t != "null"]
+
+                # If we have multiple non-null types, use VARCHAR
+                if len(non_null_types) > 1:
+                    self.handle_multiple_types(non_null_types)
+
+                # If we have exactly one non-null type, use its handler
+                if len(non_null_types) == 1 and non_null_types[0] in self._type_mapping:
+                    handler = self._type_mapping[non_null_types[0]]
+                    return self._invoke_handler(handler, schema)
+
+            elif type_handler := self._type_mapping.get(schema_type):
+                return self._invoke_handler(type_handler, schema)
+
+        return None
+
+    def _handle_format(self, schema: dict) -> sa.types.TypeEngine | None:
+        """Handle format-specific type conversion.
+
+        Args:
+            schema: The JSON Schema object.
+
+        Returns:
+            The format-specific SQL type if applicable, None otherwise.
+        """
+        if "format" not in schema:
+            return None
+
+        format_string: str = schema["format"]
+
+        if handler := self._format_handlers.get(format_string):
+            return self._invoke_handler(handler, schema)
+
+        return None
+
+    def _handle_string_type(self, schema: dict) -> sa.types.TypeEngine:
+        """Handle string type conversion with special cases for formats.
+
+        Args:
+            schema: The JSON Schema object.
+
+        Returns:
+            Appropriate SQLAlchemy type.
+        """
+        # Check for format-specific handling first
+        if format_type := self._handle_format(schema):
+            return format_type
+
+        return self.handle_raw_string(schema)
+
+    def to_sql_type(self, schema: dict) -> sa.types.TypeEngine:
+        """Convert a JSON Schema type definition to a SQLAlchemy type.
+
+        Args:
+            schema: The JSON Schema object.
+
+        Returns:
+            The corresponding SQLAlchemy type.
+        """
+        if sql_type := self._get_type_from_schema(schema):
+            return sql_type
+
+        # Handle anyOf
+        if "anyOf" in schema:
+            for subschema in schema["anyOf"]:
+                # Skip null types in anyOf
+                if subschema.get("type") == "null":
+                    continue
+
+                if sql_type := self._get_type_from_schema(subschema):
+                    return sql_type
+
+        # Fallback
+        return self.fallback_type()
+
+
 class SQLConnector:  # noqa: PLR0904
     """Base class for SQLAlchemy-based connectors.
 
@@ -255,6 +481,16 @@ def sql_to_jsonschema(self) -> SQLToJSONSchema:
         """
         return SQLToJSONSchema()
 
+    @functools.cached_property
+    def jsonschema_to_sql(self) -> JSONSchemaToSQL:
+        """The JSON-to-SQL type mapper object for this SQL connector.
+
+        Override this property to provide a custom mapping for your SQL dialect.
+
+        .. versionadded:: 0.42.0
+        """
+        return JSONSchemaToSQL()
+
     @contextmanager
     def _connect(self) -> t.Iterator[sa.engine.Connection]:
         with self._engine.connect().execution_options(stream_results=True) as conn:
@@ -418,8 +654,7 @@ def to_jsonschema_type(
         msg = f"Unexpected type received: '{type(sql_type).__name__}'"
         raise ValueError(msg)
 
-    @staticmethod
-    def to_sql_type(jsonschema_type: dict) -> sa.types.TypeEngine:
+    def to_sql_type(self, jsonschema_type: dict) -> sa.types.TypeEngine:
         """Return a JSON Schema representation of the provided type.
 
         By default will call `typing.to_sql_type()`.
@@ -435,7 +670,7 @@ def to_sql_type(jsonschema_type: dict) -> sa.types.TypeEngine:
         Returns:
             The SQLAlchemy type representation of the data type.
         """
-        return th.to_sql_type(jsonschema_type)
+        return self.jsonschema_to_sql.to_sql_type(jsonschema_type)
 
     @staticmethod
     def get_fully_qualified_name(
@@ -982,6 +1217,28 @@ def prepare_table(
                 self.to_sql_type(property_def),
             )
 
+        self.prepare_primary_key(
+            full_table_name=full_table_name,
+            primary_keys=primary_keys,
+        )
+
+    def prepare_primary_key(
+        self,
+        *,
+        full_table_name: str | FullyQualifiedName,  # noqa: ARG002
+        primary_keys: t.Sequence[str],  # noqa: ARG002
+    ) -> None:
+        """Adapt target table primary key to provided schema if possible.
+
+        Implement this method in a subclass to adapt the primary key of the target table
+        to the provided one if possible.
+
+        Args:
+            full_table_name: the target table name.
+            primary_keys: list of key properties.
+        """
+        self.logger.debug("Primary key adaptation is not implemented")
+
     def prepare_column(
         self,
         full_table_name: str | FullyQualifiedName,
diff --git a/singer_sdk/contrib/batch_encoder_jsonl.py b/singer_sdk/contrib/batch_encoder_jsonl.py
index 6f121f8d4..00ef52355 100644
--- a/singer_sdk/contrib/batch_encoder_jsonl.py
+++ b/singer_sdk/contrib/batch_encoder_jsonl.py
@@ -40,10 +40,10 @@ def get_batches(
             filename = f"{prefix}{sync_id}-{i}.json.gz"
             with self.batch_config.storage.fs(create=True) as fs:
                 # TODO: Determine compression from config.
-                with fs.open(filename, "wb") as f, gzip.GzipFile(
-                    fileobj=f,
-                    mode="wb",
-                ) as gz:
+                with (
+                    fs.open(filename, "wb") as f,
+                    gzip.GzipFile(fileobj=f, mode="wb") as gz,
+                ):
                     gz.writelines(
                         (serialize_json(record) + "\n").encode() for record in chunk
                     )
diff --git a/singer_sdk/contrib/filesystem/config.py b/singer_sdk/contrib/filesystem/config.py
index eccd11fca..ed16f067b 100644
--- a/singer_sdk/contrib/filesystem/config.py
+++ b/singer_sdk/contrib/filesystem/config.py
@@ -12,35 +12,41 @@
             "host",
             th.StringType,
             required=True,
+            title="FTP Host",
             description="FTP server host",
         ),
         th.Property(
             "port",
             th.IntegerType,
             default=21,
+            title="FTP Port",
             description="FTP server port",
         ),
         th.Property(
             "username",
             th.StringType,
+            title="FTP Username",
             description="FTP username",
         ),
         th.Property(
             "password",
             th.StringType,
             secret=True,
+            title="FTP Password",
             description="FTP password",
         ),
         th.Property(
             "timeout",
             th.IntegerType,
             default=60,
+            title="Timeout",
             description="Timeout of the FTP connection in seconds",
         ),
         th.Property(
             "encoding",
             th.StringType,
             default="utf-8",
+            title="Encoding",
             description="FTP server encoding",
         ),
     ),
@@ -56,6 +62,7 @@
             "host",
             th.StringType,
             required=True,
+            title="SFTP Host",
             description="SFTP server host",
         ),
         th.Property(
@@ -65,33 +72,39 @@
                     "port",
                     th.IntegerType,
                     default=22,
+                    title="SFTP Port",
                     description="SFTP server port",
                 ),
                 th.Property(
                     "username",
                     th.StringType,
                     required=True,
+                    title="SFTP Username",
                     description="SFTP username",
                 ),
                 th.Property(
                     "password",
                     th.StringType,
                     secret=True,
+                    title="SFTP Password",
                     description="SFTP password",
                 ),
                 th.Property(
                     "pkey",
                     th.StringType,
                     secret=True,
+                    title="SFTP Private Key",
                     description="Private key",
                 ),
                 th.Property(
                     "timeout",
                     th.IntegerType,
                     default=60,
+                    title="Timeout",
                     description="Timeout of the SFTP connection in seconds",
                 ),
             ),
+            title="SSH Connection Settings",
             description="SSH connection settings",
         ),
     ),
diff --git a/singer_sdk/contrib/filesystem/tap.py b/singer_sdk/contrib/filesystem/tap.py
index f2fd7c352..58ca673d8 100644
--- a/singer_sdk/contrib/filesystem/tap.py
+++ b/singer_sdk/contrib/filesystem/tap.py
@@ -36,18 +36,21 @@ class ReadMode(str, enum.Enum):
         required=True,
         default="local",
         allowed_values=["local", "ftp", "sftp"],
+        title="Filesystem",
         description="The filesystem to use.",
     ),
     th.Property(
         "path",
         th.StringType,
         required=True,
+        title="Directory Path",
         description="Path to the directory where the files are stored.",
     ),
     th.Property(
         "read_mode",
         th.StringType,
         required=True,
+        title="Read Mode",
         description=(
             "Use `one_stream_per_file` to read each file as a separate stream, or "
             "`merge` to merge all files into a single stream."
@@ -59,6 +62,7 @@ class ReadMode(str, enum.Enum):
         th.StringType,
         required=True,
         default=DEFAULT_MERGE_STREAM_NAME,
+        title="Stream Name (Merge Mode)",
         description="Name of the stream to use when `read_mode` is `merge`.",
     ),
     filesystem_config.FTP,
diff --git a/singer_sdk/helpers/_compat.py b/singer_sdk/helpers/_compat.py
index 2ad9528e6..b6f0ad43e 100644
--- a/singer_sdk/helpers/_compat.py
+++ b/singer_sdk/helpers/_compat.py
@@ -4,15 +4,9 @@
 
 import datetime
 import sys
+from importlib import resources as importlib_resources
 
-if sys.version_info < (3, 9):
-    import importlib_resources
-else:
-    from importlib import resources as importlib_resources
-
-if sys.version_info < (3, 9):
-    from importlib_resources.abc import Traversable
-elif sys.version_info < (3, 12):
+if sys.version_info < (3, 12):
     from importlib.abc import Traversable
 else:
     from importlib.resources.abc import Traversable
@@ -31,7 +25,13 @@
 date_fromisoformat = datetime.date.fromisoformat
 time_fromisoformat = datetime.time.fromisoformat
 
+
+class SingerSDKDeprecationWarning(DeprecationWarning):
+    """Custom deprecation warning for the Singer SDK."""
+
+
 __all__ = [
+    "SingerSDKDeprecationWarning",
     "Traversable",
     "date_fromisoformat",
     "datetime_fromisoformat",
diff --git a/singer_sdk/helpers/_state.py b/singer_sdk/helpers/_state.py
index fd7dee377..565dbd51d 100644
--- a/singer_sdk/helpers/_state.py
+++ b/singer_sdk/helpers/_state.py
@@ -218,6 +218,10 @@ def increment_state(
                 extra={"replication_key": replication_key},
             )
         progress_dict = stream_or_partition_state[PROGRESS_MARKERS]
+    # TODO: Instead of forcing all values to be JSON-compatible strings and hope
+    # we catch all cases, we should allow the stream to define how to
+    # the values from the state and the record should be pre-processed.
+    # https://github.com/meltano/sdk/issues/2753
     old_rk_value = to_json_compatible(progress_dict.get("replication_key_value"))
     new_rk_value = to_json_compatible(latest_record[replication_key])
 
diff --git a/singer_sdk/helpers/_typing.py b/singer_sdk/helpers/_typing.py
index 1e7370fd9..d3b629c11 100644
--- a/singer_sdk/helpers/_typing.py
+++ b/singer_sdk/helpers/_typing.py
@@ -6,6 +6,7 @@
 import datetime
 import logging
 import typing as t
+import uuid
 from enum import Enum
 from functools import lru_cache
 
@@ -42,6 +43,8 @@ def to_json_compatible(val: t.Any) -> t.Any:  # noqa: ANN401
     if isinstance(val, (datetime.datetime,)):
         # Make naive datetimes UTC
         return (val.replace(tzinfo=UTC) if val.tzinfo is None else val).isoformat("T")
+    if isinstance(val, (uuid.UUID,)):
+        return str(val)
     return val
 
 
@@ -279,6 +282,17 @@ def is_boolean_type(property_schema: dict) -> bool | None:
     return False
 
 
+def _is_exclusive_boolean_type(property_schema: dict) -> bool:
+    if "type" not in property_schema:
+        return False
+
+    return (
+        property_schema["type"] == "boolean"
+        or property_schema["type"] == ["boolean"]
+        or set(property_schema["type"]) == {"boolean", "null"}
+    )
+
+
 def is_integer_type(property_schema: dict) -> bool | None:
     """Return true if the JSON Schema type is an integer or None if detection fails."""
     if "anyOf" not in property_schema and "type" not in property_schema:
@@ -523,6 +537,6 @@ def _conform_primitive_property(  # noqa: PLR0911
     if isinstance(elem, bytes):
         # for BIT value, treat 0 as False and anything else as True
         return elem != b"\x00" if is_boolean_type(property_schema) else elem.hex()
-    if is_boolean_type(property_schema):
+    if _is_exclusive_boolean_type(property_schema):
         return None if elem is None else elem != 0
     return elem
diff --git a/singer_sdk/helpers/capabilities.py b/singer_sdk/helpers/capabilities.py
index 76d7fcffb..0f5c42918 100644
--- a/singer_sdk/helpers/capabilities.py
+++ b/singer_sdk/helpers/capabilities.py
@@ -26,6 +26,7 @@
     Property(
         "stream_maps",
         ObjectType(),
+        title="Stream Maps",
         description=(
             "Config object for stream maps capability. "
             "For more information check out "
@@ -35,6 +36,7 @@
     Property(
         "stream_map_config",
         ObjectType(),
+        title="User Stream Map Configuration",
         description="User-defined config values to be used within map expressions.",
     ),
     Property(
@@ -43,6 +45,7 @@
             Property(
                 "seed",
                 OneOf(NumberType, StringType, BooleanType),
+                title="Faker Seed",
                 description=(
                     "Value to seed the Faker generator for deterministic output: "
                     "https://faker.readthedocs.io/en/master/#seeding-the-generator"
@@ -51,12 +54,14 @@
             Property(
                 "locale",
                 OneOf(StringType, ArrayType(StringType)),
+                title="Faker Locale",
                 description=(
                     "One or more LCID locale strings to produce localized output for: "
                     "https://faker.readthedocs.io/en/master/#localization"
                 ),
             ),
         ),
+        title="Faker Configuration",
         description=(
             "Config for the [`Faker`](https://faker.readthedocs.io/en/master/) "
             "instance variable `fake` used within map expressions. Only applicable if "
@@ -69,6 +74,7 @@
     Property(
         "flattening_enabled",
         BooleanType(),
+        title="Enable Schema Flattening",
         description=(
             "'True' to enable schema flattening and automatically expand nested "
             "properties."
@@ -77,44 +83,52 @@
     Property(
         "flattening_max_depth",
         IntegerType(),
+        title="Max Flattening Depth",
         description="The max depth to flatten schemas.",
     ),
 ).to_dict()
 BATCH_CONFIG = PropertiesList(
     Property(
         "batch_config",
-        description="",
+        title="Batch Configuration",
+        description="Configuration for BATCH message capabilities.",
         wrapped=ObjectType(
             Property(
                 "encoding",
+                title="Batch Encoding Configuration",
                 description="Specifies the format and compression of the batch files.",
                 wrapped=ObjectType(
                     Property(
                         "format",
                         StringType,
                         allowed_values=["jsonl", "parquet"],
+                        title="Batch Encoding Format",
                         description="Format to use for batch files.",
                     ),
                     Property(
                         "compression",
                         StringType,
                         allowed_values=["gzip", "none"],
+                        title="Batch Compression Format",
                         description="Compression format to use for batch files.",
                     ),
                 ),
             ),
             Property(
                 "storage",
+                title="Batch Storage Configuration",
                 description="Defines the storage layer to use when writing batch files",
                 wrapped=ObjectType(
                     Property(
                         "root",
                         StringType,
+                        title="Batch Storage Root",
                         description="Root path to use when writing batch files.",
                     ),
                     Property(
                         "prefix",
                         StringType,
+                        title="Batch Storage Prefix",
                         description="Prefix to use when writing batch files.",
                     ),
                 ),
@@ -126,6 +140,7 @@
     Property(
         "default_target_schema",
         StringType(),
+        title="Default Target Schema",
         description="The default target database schema name to use for all streams.",
     ),
 ).to_dict()
@@ -133,13 +148,15 @@
     Property(
         "add_record_metadata",
         BooleanType(),
-        description="Add metadata to records.",
+        title="Add Record Metadata",
+        description="Whether to add metadata fields to records.",
     ),
 ).to_dict()
 TARGET_HARD_DELETE_CONFIG = PropertiesList(
     Property(
         "hard_delete",
         BooleanType(),
+        title="Hard Delete",
         description="Hard delete records.",
         default=False,
     ),
@@ -148,6 +165,7 @@
     Property(
         "validate_records",
         BooleanType(),
+        title="Validate Records",
         description="Whether to validate the schema of the incoming streams.",
         default=True,
     ),
@@ -156,6 +174,7 @@
     Property(
         "batch_size_rows",
         IntegerType,
+        title="Batch Size Rows",
         description="Maximum number of rows in each batch.",
     ),
 ).to_dict()
diff --git a/singer_sdk/helpers/types.py b/singer_sdk/helpers/types.py
index 6d8c877ff..7693b17d4 100644
--- a/singer_sdk/helpers/types.py
+++ b/singer_sdk/helpers/types.py
@@ -4,14 +4,10 @@
 
 import sys
 import typing as t
+from collections.abc import Mapping
 
 import requests
 
-if sys.version_info < (3, 9):
-    from typing import Mapping  # noqa: ICN003
-else:
-    from collections.abc import Mapping
-
 if sys.version_info < (3, 10):
     from typing_extensions import TypeAlias
 else:
@@ -24,5 +20,5 @@
 ]
 
 Context: TypeAlias = Mapping[str, t.Any]
-Record: TypeAlias = t.Dict[str, t.Any]
+Record: TypeAlias = dict[str, t.Any]
 Auth: TypeAlias = t.Callable[[requests.PreparedRequest], requests.PreparedRequest]
diff --git a/singer_sdk/mapper.py b/singer_sdk/mapper.py
index b613b78ec..004d0f60a 100644
--- a/singer_sdk/mapper.py
+++ b/singer_sdk/mapper.py
@@ -63,7 +63,7 @@ def md5(string: str) -> str:
     return hashlib.md5(string.encode("utf-8")).hexdigest()  # noqa: S324
 
 
-StreamMapsDict: TypeAlias = t.Dict[str, t.Union[str, dict, None]]
+StreamMapsDict: TypeAlias = dict[str, t.Union[str, dict, None]]
 
 
 class StreamMap(metaclass=abc.ABCMeta):
@@ -337,6 +337,7 @@ def _eval(
         names["_"] = record  # Add a shorthand alias in case of reserved words in names
         names["record"] = record  # ...and a longhand alias
         names["config"] = self.map_config  # Allow map config access within transform
+        names["__stream_name__"] = self.stream_alias  # Access stream name in transform
 
         if self.fake:
             from faker import Faker  # noqa: PLC0415
@@ -400,10 +401,12 @@ def _eval_type(  # noqa: PLR0911
         if expr.startswith("bool("):
             return th.BooleanType()
 
-        if expr.startswith("datetime.date") or expr.endswith(".date()"):
+        if expr.startswith(("datetime.date.", "datetime.date(")) or expr.endswith(
+            ".date()"
+        ):
             return th.DateType()
 
-        if expr.startswith("datetime.datetime"):
+        if expr.startswith(("datetime.datetime.", "datetime.datetime(")):
             return th.DateTimeType()
 
         return th.StringType() if expr[0] == "'" and expr[-1] == "'" else default
@@ -779,6 +782,7 @@ def register_raw_stream_schema(  # noqa: PLR0912, C901
                 elif MAPPER_ALIAS_OPTION in stream_def:
                     # <source>: __alias__: <alias>
                     stream_alias = stream_def.pop(MAPPER_ALIAS_OPTION)
+                    stream_alias = PluginMapper._eval_stream(stream_alias, stream_name)
 
             if stream_name == source_stream:
                 # Exact match
@@ -831,3 +835,40 @@ def register_raw_stream_schema(  # noqa: PLR0912, C901
             else:
                 # Additional mappers for aliasing and multi-projection:
                 self.stream_maps[source_stream].append(mapper)
+
+    @staticmethod
+    def _eval_stream(expr: str, stream_name: str) -> str:
+        """Solve an alias expression.
+
+        Args:
+            expr: String expression to evaluate.
+            stream_name: Name of stream to transform.
+
+        Returns:
+            Evaluated expression.
+
+        Raises:
+            MapExpressionError: If the mapping expression failed to evaluate.
+        """
+        # Allow stream name access within alias transform
+        names = {"__stream_name__": stream_name}
+
+        result: str
+
+        try:
+            expr_evaluator = simpleeval.EvalWithCompoundTypes(names=names)
+            result = expr_evaluator.eval(expr)
+        except simpleeval.NameNotDefined:
+            logging.debug(
+                "Failed to evaluate simpleeval expression %(expr) - "
+                "falling back to original expression",
+                extra={"expr": expr},
+            )
+            result = expr
+        except (simpleeval.InvalidExpression, SyntaxError) as ex:
+            msg = f"Failed to evaluate simpleeval expressions {expr}."
+            raise MapExpressionError(msg) from ex
+
+        logging.debug("Stream eval result: %s = %s", expr, result)
+
+        return result
diff --git a/singer_sdk/mapper_base.py b/singer_sdk/mapper_base.py
index 626133787..650552f5f 100644
--- a/singer_sdk/mapper_base.py
+++ b/singer_sdk/mapper_base.py
@@ -90,7 +90,7 @@ def map_activate_version_message(
 
     def map_batch_message(  # noqa: PLR6301
         self,
-        message_dict: dict,  # noqa: ARG002
+        message_dict: dict,
     ) -> t.Iterable[singer.Message]:
         """Map a batch message to zero or more new messages.
 
diff --git a/singer_sdk/plugin_base.py b/singer_sdk/plugin_base.py
index ed37bfb3f..db16560d4 100644
--- a/singer_sdk/plugin_base.py
+++ b/singer_sdk/plugin_base.py
@@ -8,6 +8,7 @@
 import sys
 import time
 import typing as t
+import warnings
 from importlib import metadata
 from pathlib import Path, PurePath
 from types import MappingProxyType
@@ -22,6 +23,7 @@
 )
 from singer_sdk.exceptions import ConfigValidationError
 from singer_sdk.helpers._classproperty import classproperty
+from singer_sdk.helpers._compat import SingerSDKDeprecationWarning
 from singer_sdk.helpers._secrets import SecretString, is_common_secret_key
 from singer_sdk.helpers._util import read_json_file
 from singer_sdk.helpers.capabilities import (
@@ -144,12 +146,24 @@ def __init__(
             config_dict = {}
         elif isinstance(config, (str, PurePath)):
             config_dict = read_json_file(config)
+            warnings.warn(
+                "Passsing a config file path is deprecated. Please pass the config "
+                "as a dictionary instead.",
+                SingerSDKDeprecationWarning,
+                stacklevel=2,
+            )
         elif isinstance(config, list):
             config_dict = {}
             for config_path in config:
                 # Read each config file sequentially. Settings from files later in the
                 # list will override those of earlier ones.
                 config_dict.update(read_json_file(config_path))
+            warnings.warn(
+                "Passsing a list of config file paths is deprecated. Please pass the "
+                "config as a dictionary instead.",
+                SingerSDKDeprecationWarning,
+                stacklevel=2,
+            )
         elif isinstance(config, dict):
             config_dict = config
         else:
diff --git a/singer_sdk/sinks/core.py b/singer_sdk/sinks/core.py
index 7bbed6497..5070655d4 100644
--- a/singer_sdk/sinks/core.py
+++ b/singer_sdk/sinks/core.py
@@ -739,10 +739,10 @@ def process_batch_files(
                 storage = StorageTarget.from_url(head)
 
             if encoding.format == BatchFileFormat.JSONL:
-                with storage.fs(create=False) as batch_fs, batch_fs.open(
-                    tail,
-                    mode="rb",
-                ) as file:
+                with (
+                    storage.fs(create=False) as batch_fs,
+                    batch_fs.open(tail, mode="rb") as file,
+                ):
                     if encoding.compression == "gzip":
                         with gzip_open(file) as context_file:
                             context = {
@@ -760,10 +760,10 @@ def process_batch_files(
             ):
                 import pyarrow.parquet as pq  # noqa: PLC0415
 
-                with storage.fs(create=False) as batch_fs, batch_fs.open(
-                    tail,
-                    mode="rb",
-                ) as file:
+                with (
+                    storage.fs(create=False) as batch_fs,
+                    batch_fs.open(tail, mode="rb") as file,
+                ):
                     table = pq.read_table(file)
                     context = {"records": table.to_pylist()}
                     self.record_counter_metric.increment(len(context["records"]))
diff --git a/singer_sdk/sinks/sql.py b/singer_sdk/sinks/sql.py
index 0f7695ef0..5bb64afad 100644
--- a/singer_sdk/sinks/sql.py
+++ b/singer_sdk/sinks/sql.py
@@ -292,7 +292,7 @@ def generate_insert_statement(
             INSERT INTO {full_table_name}
             ({", ".join(column_identifiers)})
             VALUES ({", ".join([f":{name}" for name in property_names])})
-            """,  # noqa: S608
+            """,
         )
         return statement.rstrip()
 
diff --git a/singer_sdk/streams/core.py b/singer_sdk/streams/core.py
index 550b99809..009726b7f 100644
--- a/singer_sdk/streams/core.py
+++ b/singer_sdk/streams/core.py
@@ -7,6 +7,7 @@
 import datetime
 import json
 import typing as t
+import warnings
 from os import PathLike
 from pathlib import Path
 from types import MappingProxyType
@@ -27,7 +28,10 @@
     SDKBatchMessage,
 )
 from singer_sdk.helpers._catalog import pop_deselected_record_properties
-from singer_sdk.helpers._compat import datetime_fromisoformat
+from singer_sdk.helpers._compat import (
+    SingerSDKDeprecationWarning,
+    datetime_fromisoformat,
+)
 from singer_sdk.helpers._flattening import get_flattening_options
 from singer_sdk.helpers._state import (
     finalize_state_progress_markers,
@@ -157,6 +161,12 @@ def __init__(
                     raise FileNotFoundError(msg)
 
                 self._schema_filepath = Path(schema)
+                warnings.warn(
+                    "Passing a schema filepath is deprecated. Please pass the schema "
+                    "dictionary or a Singer Schema object instead.",
+                    SingerSDKDeprecationWarning,
+                    stacklevel=2,
+                )
             elif isinstance(schema, dict):
                 self._schema = schema
             elif isinstance(schema, singer.Schema):
diff --git a/singer_sdk/streams/rest.py b/singer_sdk/streams/rest.py
index 7f1f6fb89..dcfdf7104 100644
--- a/singer_sdk/streams/rest.py
+++ b/singer_sdk/streams/rest.py
@@ -5,6 +5,7 @@
 import abc
 import copy
 import logging
+import sys
 import typing as t
 from functools import cached_property
 from http import HTTPStatus
@@ -17,6 +18,7 @@
 from singer_sdk import metrics
 from singer_sdk.authenticators import SimpleAuthenticator
 from singer_sdk.exceptions import FatalAPIError, RetriableAPIError
+from singer_sdk.helpers._compat import SingerSDKDeprecationWarning
 from singer_sdk.helpers.jsonpath import extract_jsonpath
 from singer_sdk.pagination import (
     BaseAPIPaginator,
@@ -26,7 +28,13 @@
 )
 from singer_sdk.streams.core import Stream
 
+if sys.version_info < (3, 13):
+    from typing_extensions import deprecated
+else:
+    from warnings import deprecated  # pragma: no cover
+
 if t.TYPE_CHECKING:
+    from collections.abc import Iterable, Mapping
     from datetime import datetime
 
     from backoff.types import Details
@@ -41,28 +49,21 @@
 _TToken = t.TypeVar("_TToken")
 
 
-class RESTStream(Stream, t.Generic[_TToken], metaclass=abc.ABCMeta):  # noqa: PLR0904
-    """Abstract base class for REST API streams."""
+class _HTTPStream(Stream, t.Generic[_TToken], metaclass=abc.ABCMeta):  # noqa: PLR0904
+    """Abstract base class for HTTP streams."""
 
     _page_size: int = DEFAULT_PAGE_SIZE
     _requests_session: requests.Session | None
 
-    #: HTTP method to use for requests. Defaults to "GET".
-    rest_method = "GET"
-
-    #: JSONPath expression to extract records from the API response.
-    records_jsonpath: str = "$[*]"
-
     #: Response code reference for rate limit retries
     extra_retry_statuses: t.Sequence[int] = [HTTPStatus.TOO_MANY_REQUESTS]
 
-    #: Optional JSONPath expression to extract a pagination token from the API response.
-    #: Example: `"$.next_page"`
-    next_page_token_jsonpath: str | None = None
-
     #: Optional flag to disable HTTP redirects. Defaults to False.
     allow_redirects: bool = True
 
+    #: Set this to True if the API expects a JSON payload in the request body.
+    payload_as_json: bool = False
+
     # Private constants. May not be supported in future releases:
     _LOG_REQUEST_METRICS: bool = True
     # Disabled by default for safety:
@@ -90,7 +91,7 @@ def __init__(
         schema: dict[str, t.Any] | Schema | None = None,
         path: str | None = None,
     ) -> None:
-        """Initialize the REST stream.
+        """Initialize the HTTP stream.
 
         Args:
             tap: Singer Tap this stream belongs to.
@@ -103,8 +104,6 @@ def __init__(
             self.path = path
         self._http_headers: dict = {"User-Agent": self.user_agent}
         self._requests_session = requests.Session()
-        self._compiled_jsonpath = None
-        self._next_page_token_compiled_jsonpath = None
 
     @staticmethod
     def _url_encode(val: str | datetime | bool | int | list[str]) -> str:  # noqa: FBT001
@@ -140,6 +139,24 @@ def get_url(self, context: Context | None) -> str:
 
     # HTTP Request functions
 
+    @property
+    @deprecated(
+        "Use `http_method` instead.",
+        category=SingerSDKDeprecationWarning,
+    )
+    def rest_method(self) -> str:
+        """HTTP method to use for requests. Defaults to "GET".
+
+        .. deprecated:: 0.43.0
+           Override :meth:`~singer_sdk.RESTStream.http_method` instead.
+        """
+        return "GET"
+
+    @property
+    def http_method(self) -> str:
+        """HTTP method to use for requests. Defaults to "GET"."""
+        return self.rest_method
+
     @property
     def requests_session(self) -> requests.Session:
         """Get requests session.
@@ -369,19 +386,25 @@ def prepare_request(
             Build a request with the stream's URL, path, query parameters,
             HTTP headers and authenticator.
         """
-        http_method = self.rest_method
+        http_method = self.http_method
         url: str = self.get_url(context)
         params: dict | str = self.get_url_params(context, next_page_token)
         request_data = self.prepare_request_payload(context, next_page_token)
         headers = self.http_headers
 
-        return self.build_prepared_request(
-            method=http_method,
-            url=url,
-            params=params,
-            headers=headers,
-            json=request_data,
-        )
+        prepare_kwargs: dict[str, t.Any] = {
+            "method": http_method,
+            "url": url,
+            "params": params,
+            "headers": headers,
+        }
+
+        if self.payload_as_json:
+            prepare_kwargs["json"] = request_data
+        else:
+            prepare_kwargs["data"] = request_data
+
+        return self.build_prepared_request(**prepare_kwargs)
 
     def request_records(self, context: Context | None) -> t.Iterable[dict]:
         """Request records from REST endpoint(s), returning response records.
@@ -522,8 +545,16 @@ def prepare_request_payload(
         self,
         context: Context | None,
         next_page_token: _TToken | None,
-    ) -> dict | None:
-        """Prepare the data payload for the REST API request.
+    ) -> (
+        Iterable[bytes]
+        | str
+        | bytes
+        | list[tuple[t.Any, t.Any]]
+        | tuple[tuple[t.Any, t.Any]]
+        | Mapping[str, t.Any]
+        | None
+    ):
+        """Prepare the data payload for the HTTP request.
 
         By default, no payload will be sent (return None).
 
@@ -537,27 +568,6 @@ def prepare_request_payload(
                 next page of data.
         """
 
-    def get_new_paginator(self) -> BaseAPIPaginator:
-        """Get a fresh paginator for this API endpoint.
-
-        Returns:
-            A paginator instance.
-        """
-        if hasattr(self, "get_next_page_token"):
-            warn(
-                "`RESTStream.get_next_page_token` is deprecated and will not be used "
-                "in a future version of the Meltano Singer SDK. "
-                "Override `RESTStream.get_new_paginator` instead.",
-                DeprecationWarning,
-                stacklevel=2,
-            )
-            return LegacyStreamPaginator(self)
-
-        if self.next_page_token_jsonpath:
-            return JSONPathPaginator(self.next_page_token_jsonpath)
-
-        return SimpleHeaderPaginator("X-Next-Page")
-
     @property
     def http_headers(self) -> dict:
         """Return headers dict to be used for HTTP requests.
@@ -601,6 +611,9 @@ def get_records(self, context: Context | None) -> t.Iterable[dict[str, t.Any]]:
                 continue
             yield transformed_record
 
+    # Abstract methods:
+
+    @abc.abstractmethod
     def parse_response(self, response: requests.Response) -> t.Iterable[dict]:
         """Parse the response and return an iterator of result records.
 
@@ -610,9 +623,16 @@ def parse_response(self, response: requests.Response) -> t.Iterable[dict]:
         Yields:
             One item for every item found in the response.
         """
-        yield from extract_jsonpath(self.records_jsonpath, input=response.json())
+        ...
 
-    # Abstract methods:
+    @abc.abstractmethod
+    def get_new_paginator(self) -> BaseAPIPaginator:
+        """Get a fresh paginator for this endpoint.
+
+        Returns:
+            A paginator instance.
+        """
+        ...
 
     @property
     def authenticator(self) -> Auth:
@@ -712,3 +732,72 @@ def backoff_runtime(  # noqa: PLR6301
         exception = yield  # type: ignore[misc]
         while True:
             exception = yield value(exception)
+
+
+class RESTStream(_HTTPStream, t.Generic[_TToken], metaclass=abc.ABCMeta):
+    """Abstract base class for REST API streams."""
+
+    #: JSONPath expression to extract records from the API response.
+    records_jsonpath: str = "$[*]"
+
+    #: Optional JSONPath expression to extract a pagination token from the API response.
+    #: Example: `"$.next_page"`
+    next_page_token_jsonpath: str | None = None
+
+    payload_as_json: bool = True
+    """Set this to False if the API expects something other than JSON in the request
+    body.
+
+    .. versionadded:: 0.43.0
+    """
+
+    def __init__(
+        self,
+        tap: Tap,
+        name: str | None = None,
+        schema: dict[str, t.Any] | Schema | None = None,
+        path: str | None = None,
+    ) -> None:
+        """Initialize the REST stream.
+
+        Args:
+            tap: Singer Tap this stream belongs to.
+            schema: JSON schema for records in this stream.
+            name: Name of this stream.
+            path: URL path for this entity stream.
+        """
+        super().__init__(tap, name, schema, path)
+        self._compiled_jsonpath = None
+        self._next_page_token_compiled_jsonpath = None
+
+    def parse_response(self, response: requests.Response) -> t.Iterable[dict]:
+        """Parse the response and return an iterator of result records.
+
+        Args:
+            response: A raw :class:`requests.Response`
+
+        Yields:
+            One item for every item found in the response.
+        """
+        yield from extract_jsonpath(self.records_jsonpath, input=response.json())
+
+    def get_new_paginator(self) -> BaseAPIPaginator:
+        """Get a fresh paginator for this API endpoint.
+
+        Returns:
+            A paginator instance.
+        """
+        if hasattr(self, "get_next_page_token"):
+            warn(
+                "`RESTStream.get_next_page_token` is deprecated and will not be used "
+                "in a future version of the Meltano Singer SDK. "
+                "Override `RESTStream.get_new_paginator` instead.",
+                DeprecationWarning,
+                stacklevel=2,
+            )
+            return LegacyStreamPaginator(self)
+
+        if self.next_page_token_jsonpath:
+            return JSONPathPaginator(self.next_page_token_jsonpath)
+
+        return SimpleHeaderPaginator("X-Next-Page")
diff --git a/singer_sdk/tap_base.py b/singer_sdk/tap_base.py
index d246a2790..82900049c 100644
--- a/singer_sdk/tap_base.py
+++ b/singer_sdk/tap_base.py
@@ -5,6 +5,7 @@
 import abc
 import contextlib
 import typing as t
+import warnings
 from enum import Enum
 
 import click
@@ -18,6 +19,7 @@
 )
 from singer_sdk.helpers import _state
 from singer_sdk.helpers._classproperty import classproperty
+from singer_sdk.helpers._compat import SingerSDKDeprecationWarning
 from singer_sdk.helpers._state import write_stream_state
 from singer_sdk.helpers._util import dump_json, read_json_file
 from singer_sdk.helpers.capabilities import (
@@ -102,6 +104,12 @@ def __init__(
             self._input_catalog = Catalog.from_dict(catalog)  # type: ignore[arg-type]
         elif catalog is not None:
             self._input_catalog = Catalog.from_dict(read_json_file(catalog))
+            warnings.warn(
+                "Passsing a catalog file path is deprecated. Please pass the catalog "
+                "as a dictionary or Catalog object instead.",
+                SingerSDKDeprecationWarning,
+                stacklevel=2,
+            )
 
         self._mapper: PluginMapper | None = None
 
@@ -114,6 +122,12 @@ def __init__(
             state_dict = state
         elif state:
             state_dict = read_json_file(state)
+            warnings.warn(
+                "Passsing a state file path is deprecated. Please pass the state "
+                "as a dictionary instead.",
+                SingerSDKDeprecationWarning,
+                stacklevel=2,
+            )
         self.load_state(state_dict)
 
     # Class properties
diff --git a/singer_sdk/testing/suites.py b/singer_sdk/testing/suites.py
index fd53e6e19..a61268759 100644
--- a/singer_sdk/testing/suites.py
+++ b/singer_sdk/testing/suites.py
@@ -36,6 +36,7 @@
     TargetInvalidSchemaTest,
     TargetNoPrimaryKeys,
     TargetOptionalAttributes,
+    TargetPrimaryKeyUpdates,
     TargetRecordBeforeSchemaTest,
     TargetRecordMissingKeyProperty,
     TargetRecordMissingOptionalFields,
@@ -104,6 +105,7 @@ class TestSuite(t.Generic[T]):
         # TargetMultipleStateMessages,
         TargetNoPrimaryKeys,
         TargetOptionalAttributes,
+        TargetPrimaryKeyUpdates,
         TargetRecordBeforeSchemaTest,
         TargetRecordMissingKeyProperty,
         TargetRecordMissingOptionalFields,
diff --git a/singer_sdk/testing/tap_tests.py b/singer_sdk/testing/tap_tests.py
index 92e0b13e1..54352c694 100644
--- a/singer_sdk/testing/tap_tests.py
+++ b/singer_sdk/testing/tap_tests.py
@@ -43,7 +43,7 @@ def test(self) -> None:
         catalog = tap1.catalog_dict
         # Reset and re-initialize with discovered catalog
         kwargs = {k: v for k, v in self.runner.default_kwargs.items() if k != "catalog"}
-        tap2: Tap = t.cast(t.Type[Tap], self.runner.singer_class)(
+        tap2: Tap = t.cast(type[Tap], self.runner.singer_class)(
             config=self.runner.config,
             catalog=catalog,
             **kwargs,
diff --git a/singer_sdk/testing/target_test_streams/pk_updates.singer b/singer_sdk/testing/target_test_streams/pk_updates.singer
new file mode 100644
index 000000000..c9b920599
--- /dev/null
+++ b/singer_sdk/testing/target_test_streams/pk_updates.singer
@@ -0,0 +1,4 @@
+{"type": "SCHEMA", "stream": "example_stream", "schema": {"properties": {"id": {"type": "integer"}, "name": {"type": "string"}, "email": {"type": "string"}}, "key_properties": ["id"]}}
+{"type": "RECORD", "stream": "example_stream", "record": {"id": 1, "name": "Alice", "email": "alice@example.com"}}
+{"type": "SCHEMA", "stream": "example_stream", "schema": {"properties": {"id": {"type": "integer"}, "name": {"type": "string"}, "email": {"type": "string"}}, "key_properties": ["email"]}}
+{"type": "RECORD", "stream": "example_stream", "record": {"id": 2, "name": "Bob", "email": "bob@example.com"}}
diff --git a/singer_sdk/testing/target_tests.py b/singer_sdk/testing/target_tests.py
index 96e0b0d59..c9d5b94de 100644
--- a/singer_sdk/testing/target_tests.py
+++ b/singer_sdk/testing/target_tests.py
@@ -135,6 +135,12 @@ class TargetSchemaUpdates(TargetFileTestTemplate):
     name = "schema_updates"
 
 
+class TargetPrimaryKeyUpdates(TargetFileTestTemplate):
+    """Test Target handles Primary Key updates."""
+
+    name = "pk_updates"
+
+
 class TargetSpecialCharsInAttributes(TargetFileTestTemplate):
     """Test Target handles special chars in attributes."""
 
diff --git a/singer_sdk/testing/templates.py b/singer_sdk/testing/templates.py
index 259811057..8a21f639c 100644
--- a/singer_sdk/testing/templates.py
+++ b/singer_sdk/testing/templates.py
@@ -3,10 +3,10 @@
 from __future__ import annotations
 
 import contextlib
+import importlib.resources
 import typing as t
 import warnings
 
-from singer_sdk.helpers._compat import importlib_resources
 from singer_sdk.testing import target_test_streams
 
 if t.TYPE_CHECKING:
@@ -249,9 +249,9 @@ def non_null_attribute_values(self) -> list[t.Any]:
     @classmethod
     def evaluate(
         cls,
-        stream: Stream,  # noqa: ARG003
-        property_name: str,  # noqa: ARG003
-        property_schema: dict,  # noqa: ARG003
+        stream: Stream,
+        property_name: str,
+        property_schema: dict,
     ) -> bool:
         """Determine if this attribute test is applicable to the given property.
 
@@ -337,4 +337,4 @@ def singer_filepath(self) -> Traversable:
         Returns:
             The expected Path to this tests singer file.
         """
-        return importlib_resources.files(target_test_streams) / f"{self.name}.singer"
+        return importlib.resources.files(target_test_streams) / f"{self.name}.singer"
diff --git a/singer_sdk/typing.py b/singer_sdk/typing.py
index d4cfd46cd..d1fe530d6 100644
--- a/singer_sdk/typing.py
+++ b/singer_sdk/typing.py
@@ -206,15 +206,18 @@ def __init__(
         *,
         allowed_values: list[T] | None = None,
         examples: list[T] | None = None,
+        nullable: bool | None = None,
     ) -> None:
         """Initialize the type helper.
 
         Args:
             allowed_values: A list of allowed values.
             examples: A list of example values.
+            nullable: If True, the property may be null.
         """
         self.allowed_values = allowed_values
         self.examples = examples
+        self.nullable = nullable
 
     @DefaultInstanceProperty
     def type_dict(self) -> dict:
@@ -273,6 +276,8 @@ class StringType(JSONTypeHelper[str]):
         {'type': ['string'], 'enum': ['a', 'b']}
         >>> StringType(max_length=10).type_dict
         {'type': ['string'], 'maxLength': 10}
+        >>> StringType(max_length=10, nullable=True).type_dict
+        {'type': ['string', 'null'], 'maxLength': 10}
     """
 
     string_format: str | None = None
@@ -321,7 +326,7 @@ def type_dict(self) -> dict:
             A dictionary describing the type.
         """
         result = {
-            "type": ["string"],
+            "type": ["string", "null"] if self.nullable else ["string"],
             **self._format,
             **self.extras,
         }
@@ -460,7 +465,10 @@ def type_dict(self) -> dict:
         Returns:
             A dictionary describing the type.
         """
-        return {"type": ["boolean"], **self.extras}
+        return {
+            "type": ["boolean", "null"] if self.nullable else ["boolean"],
+            **self.extras,
+        }
 
 
 class _NumericType(JSONTypeHelper[T]):
@@ -507,7 +515,12 @@ def type_dict(self) -> dict:
         Returns:
             A dictionary describing the type.
         """
-        result = {"type": [self.__type_name__], **self.extras}
+        result = {
+            "type": [self.__type_name__, "null"]
+            if self.nullable
+            else [self.__type_name__],
+            **self.extras,
+        }
 
         if self.minimum is not None:
             result["minimum"] = self.minimum
@@ -592,7 +605,11 @@ def type_dict(self) -> dict:  # type: ignore[override]
         Returns:
             A dictionary describing the type.
         """
-        return {"type": "array", "items": self.wrapped_type.type_dict, **self.extras}
+        return {
+            "type": ["array", "null"] if self.nullable else "array",
+            "items": self.wrapped_type.type_dict,
+            **self.extras,
+        }
 
 
 class AnyType(JSONTypeHelper):
@@ -619,7 +636,7 @@ class Property(JSONTypeHelper[T], t.Generic[T]):
     """Generic Property. Should be nested within a `PropertiesList`."""
 
     # TODO: Make some of these arguments keyword-only. This is a breaking change.
-    def __init__(
+    def __init__(  # noqa: PLR0913
         self,
         name: str,
         wrapped: JSONTypeHelper[T] | type[JSONTypeHelper[T]],
@@ -631,6 +648,7 @@ def __init__(
         examples: list[T] | None = None,
         *,
         nullable: bool | None = None,
+        title: str | None = None,
     ) -> None:
         """Initialize Property object.
 
@@ -652,6 +670,7 @@ def __init__(
             examples: Optional. A list of one or more sample values. These may be
                 displayed to the user as hints of the expected format of inputs.
             nullable: If True, the property may be null.
+            title: Optional. A short, human-readable title for the property.
         """
         self.name = name
         self.wrapped = wrapped
@@ -662,6 +681,7 @@ def __init__(
         self.allowed_values = allowed_values or None
         self.examples = examples or None
         self.nullable = nullable
+        self.title = title
 
     @property
     def type_dict(self) -> dict:  # type: ignore[override]
@@ -690,8 +710,18 @@ def to_dict(self) -> dict:
 
         Returns:
             A JSON Schema dictionary describing the object.
+
+        Examples:
+            >>> p = Property("name", StringType, required=True)
+            >>> print(p.to_dict())
+            {'name': {'type': ['string']}}
+            >>> p = Property("name", StringType, required=True, title="App Name")
+            >>> print(p.to_dict())
+            {'name': {'type': ['string'], 'title': 'App Name'}}
         """
         type_dict = self.type_dict
+        if self.title:
+            type_dict.update({"title": self.title})
         if self.nullable or self.optional:
             type_dict = append_type(type_dict, "null")
         if self.default is not None:
@@ -822,7 +852,10 @@ def type_dict(self) -> dict:  # type: ignore[override]
             merged_props.update(w.to_dict())
             if not w.optional:
                 required.append(w.name)
-        result: dict[str, t.Any] = {"type": "object", "properties": merged_props}
+        result: dict[str, t.Any] = {
+            "type": ["object", "null"] if self.nullable else "object",
+            "properties": merged_props,
+        }
 
         if required:
             result["required"] = required
@@ -1172,6 +1205,10 @@ def _jsonschema_type_check(jsonschema_type: dict, type_check: tuple[str]) -> boo
     )
 
 
+@deprecated(
+    "Use `JSONSchemaToSQL` instead.",
+    category=DeprecationWarning,
+)
 def to_sql_type(  # noqa: PLR0911, C901
     jsonschema_type: dict,
 ) -> sa.types.TypeEngine:
@@ -1183,6 +1220,12 @@ def to_sql_type(  # noqa: PLR0911, C901
     Returns:
         The SQL type.
     """
+    if _jsonschema_type_check(jsonschema_type, ("object",)):
+        return sa.types.VARCHAR()
+
+    if _jsonschema_type_check(jsonschema_type, ("array",)):
+        return sa.types.VARCHAR()
+
     if _jsonschema_type_check(jsonschema_type, ("string",)):
         datelike_type = get_datelike_property_type(jsonschema_type)
         if datelike_type:
@@ -1203,10 +1246,4 @@ def to_sql_type(  # noqa: PLR0911, C901
     if _jsonschema_type_check(jsonschema_type, ("boolean",)):
         return sa.types.BOOLEAN()
 
-    if _jsonschema_type_check(jsonschema_type, ("object",)):
-        return sa.types.VARCHAR()
-
-    if _jsonschema_type_check(jsonschema_type, ("array",)):
-        return sa.types.VARCHAR()
-
     return sa.types.VARCHAR()
diff --git a/tests/conftest.py b/tests/conftest.py
index 0b5bc4b74..ae629dee8 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -8,7 +8,6 @@
 import typing as t
 
 import pytest
-import sqlalchemy as sa
 
 from singer_sdk import SQLConnector
 from singer_sdk import typing as th
@@ -44,11 +43,6 @@ def pytest_runtest_setup(item):
         pytest.skip(f"cannot run on platform {system}")
 
 
-def pytest_report_header() -> list[str]:
-    """Return a list of strings to be displayed in the header of the report."""
-    return [f"sqlalchemy: {sa.__version__}"]
-
-
 @pytest.fixture(autouse=True)
 def _reset_envvars(monkeypatch: pytest.MonkeyPatch):
     """Remove envvars that might interfere with tests."""
diff --git a/tests/core/configuration/test_dict_config.py b/tests/core/configuration/test_dict_config.py
index 136b72e72..f3a48ac4e 100644
--- a/tests/core/configuration/test_dict_config.py
+++ b/tests/core/configuration/test_dict_config.py
@@ -1,6 +1,8 @@
 from __future__ import annotations
 
 import json
+import logging
+import typing as t
 from pathlib import Path
 
 import pytest
@@ -11,10 +13,23 @@
     parse_environment_config,
 )
 
+if t.TYPE_CHECKING:
+    from pytest_subtests import SubTests
+
 CONFIG_JSONSCHEMA = th.PropertiesList(
     th.Property("prop1", th.StringType, required=True),
     th.Property("prop2", th.StringType),
     th.Property("prop3", th.ArrayType(th.StringType)),
+    th.Property("prop4", th.IntegerType),
+    th.Property("prop5", th.BooleanType),
+    th.Property("prop6", th.ArrayType(th.IntegerType)),
+    th.Property(
+        "prop7",
+        th.ObjectType(
+            th.Property("sub_prop1", th.StringType),
+            th.Property("sub_prop2", th.IntegerType),
+        ),
+    ),
 ).to_dict()
 
 
@@ -36,30 +51,76 @@ def config_file2(tmpdir) -> str:
     return filepath
 
 
-def test_get_env_var_config(monkeypatch: pytest.MonkeyPatch):
+def test_get_env_var_config(
+    monkeypatch: pytest.MonkeyPatch,
+    subtests: SubTests,
+    caplog: pytest.LogCaptureFixture,
+):
     """Test settings parsing from environment variables."""
     with monkeypatch.context() as m:
         m.setenv("PLUGIN_TEST_PROP1", "hello")
-        m.setenv("PLUGIN_TEST_PROP3", "val1,val2")
-        m.setenv("PLUGIN_TEST_PROP4", "not-a-tap-setting")
+        m.setenv("PLUGIN_TEST_PROP3", '["val1","val2"]')
+        m.setenv("PLUGIN_TEST_PROP4", "123")
+        m.setenv("PLUGIN_TEST_PROP5", "TRUE")
+        m.setenv("PLUGIN_TEST_PROP6", "[1,2,3]")
+        m.setenv("PLUGIN_TEST_PROP7", '{"sub_prop1": "hello", "sub_prop2": 123}')
+        m.setenv("PLUGIN_TEST_PROP999", "not-a-tap-setting")
         env_config = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-        assert env_config["prop1"] == "hello"
-        assert env_config["prop3"] == ["val1", "val2"]
-        assert "PROP1" not in env_config
-        assert "prop2" not in env_config
-        assert "PROP2" not in env_config
-        assert "prop4" not in env_config
-        assert "PROP4" not in env_config
+
+        with subtests.test(msg="Parse string from environment"):
+            assert env_config["prop1"] == "hello"
+
+        with subtests.test(msg="Parse array from environment"):
+            assert env_config["prop3"] == ["val1", "val2"]
+
+        with subtests.test(msg="Parse integer from environment"):
+            assert env_config["prop4"] == 123
+
+        with subtests.test(msg="Parse boolean from environment"):
+            assert env_config["prop5"] is True
+
+        with subtests.test(msg="Parse array of integers from environment"):
+            assert env_config["prop6"] == [1, 2, 3]
+
+        with subtests.test(msg="Parse object from environment"):
+            assert env_config["prop7"] == {"sub_prop1": "hello", "sub_prop2": 123}
+
+        with subtests.test(msg="Ignore non-tap setting"):
+            missing_props = {"PROP1", "prop2", "PROP2", "prop999", "PROP999"}
+            assert not set.intersection(missing_props, env_config)
+
+        m.setenv("PLUGIN_TEST_PROP3", "val1,val2")
+        with (
+            subtests.test(msg="Legacy array parsing"),
+            caplog.at_level(logging.WARNING),
+        ):
+            parsed = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
+            assert parsed["prop3"] == ["val1", "val2"]
+
+            assert any(
+                "Parsing array of the form 'x,y,z'" in log.message
+                for log in caplog.records
+            )
 
     no_env_config = parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-    assert "prop1" not in no_env_config
-    assert "PROP1" not in env_config
-    assert "prop2" not in no_env_config
-    assert "PROP2" not in env_config
-    assert "prop3" not in no_env_config
-    assert "PROP3" not in env_config
-    assert "prop4" not in no_env_config
-    assert "PROP4" not in env_config
+    missing_props = {
+        "prop1",
+        "PROP1",
+        "prop2",
+        "PROP2",
+        "prop3",
+        "PROP3",
+        "prop4",
+        "PROP4",
+        "prop5",
+        "PROP5",
+        "prop6",
+        "PROP6",
+        "prop999",
+        "PROP999",
+    }
+    with subtests.test(msg="Ignore missing environment variables"):
+        assert not set.intersection(missing_props, no_env_config)
 
 
 def test_get_dotenv_config(tmp_path: Path):
@@ -74,15 +135,6 @@ def test_get_dotenv_config(tmp_path: Path):
     assert dotenv_config["prop1"] == "hello"
 
 
-def test_get_env_var_config_not_parsable(monkeypatch: pytest.MonkeyPatch):
-    """Test settings parsing from environment variables with a non-parsable value."""
-    with monkeypatch.context() as m:
-        m.setenv("PLUGIN_TEST_PROP1", "hello")
-        m.setenv("PLUGIN_TEST_PROP3", '["repeated"]')
-        with pytest.raises(ValueError, match="A bracketed list was detected"):
-            parse_environment_config(CONFIG_JSONSCHEMA, "PLUGIN_TEST_")
-
-
 def test_merge_config_sources(
     config_file1,
     config_file2,
@@ -91,7 +143,7 @@ def test_merge_config_sources(
     """Test merging multiple configuration sources."""
     with monkeypatch.context() as m:
         m.setenv("PLUGIN_TEST_PROP1", "from-env")
-        m.setenv("PLUGIN_TEST_PROP4", "not-a-tap-setting")
+        m.setenv("PLUGIN_TEST_PROP999", "not-a-tap-setting")
         config = merge_config_sources(
             [config_file1, config_file2, "ENV"],
             CONFIG_JSONSCHEMA,
diff --git a/tests/core/test_about.py b/tests/core/test_about.py
index 70a445bb1..5d12fed19 100644
--- a/tests/core/test_about.py
+++ b/tests/core/test_about.py
@@ -106,8 +106,8 @@ def test_get_supported_pythons_sdk():
     "specifiers,expected",
     [
         (">=3.7,<3.12", ["3.7", "3.8", "3.9", "3.10", "3.11"]),
-        (">=3.7", ["3.7", "3.8", "3.9", "3.10", "3.11", "3.12"]),
-        (">3.7", ["3.8", "3.9", "3.10", "3.11", "3.12"]),
+        (">=3.7", ["3.7", "3.8", "3.9", "3.10", "3.11", "3.12", "3.13"]),
+        (">3.7", ["3.8", "3.9", "3.10", "3.11", "3.12", "3.13"]),
         (">3.7,<=3.11", ["3.8", "3.9", "3.10", "3.11"]),
     ],
 )
diff --git a/tests/core/test_connector_sql.py b/tests/core/test_connector_sql.py
index f76f30525..a45b59373 100644
--- a/tests/core/test_connector_sql.py
+++ b/tests/core/test_connector_sql.py
@@ -11,7 +11,11 @@
 
 from samples.sample_duckdb import DuckDBConnector
 from singer_sdk.connectors import SQLConnector
-from singer_sdk.connectors.sql import FullyQualifiedName, SQLToJSONSchema
+from singer_sdk.connectors.sql import (
+    FullyQualifiedName,
+    JSONSchemaToSQL,
+    SQLToJSONSchema,
+)
 from singer_sdk.exceptions import ConfigValidationError
 
 if t.TYPE_CHECKING:
@@ -169,24 +173,25 @@ def test_deprecated_functions_warn(self, connector: SQLConnector):
             _ = connector.connection
 
     def test_connect_calls_engine(self, connector):
-        with mock.patch.object(
-            SQLConnector,
-            "_engine",
-        ) as mock_engine, connector._connect() as _:
+        with (
+            mock.patch.object(SQLConnector, "_engine") as mock_engine,
+            connector._connect() as _,
+        ):
             mock_engine.connect.assert_called_once()
 
     def test_connect_calls_connect(self, connector):
         attached_engine = connector._engine
-        with mock.patch.object(
-            attached_engine,
-            "connect",
-        ) as mock_conn, connector._connect() as _:
+        with (
+            mock.patch.object(attached_engine, "connect") as mock_conn,
+            connector._connect() as _,
+        ):
             mock_conn.assert_called_once()
 
     def test_connect_raises_on_operational_failure(self, connector):
-        with pytest.raises(
-            sa.exc.OperationalError,
-        ) as _, connector._connect() as conn:
+        with (
+            pytest.raises(sa.exc.OperationalError) as _,
+            connector._connect() as conn,
+        ):
             conn.execute(sa.text("SELECT * FROM fake_table"))
 
     def test_rename_column_uses_connect_correctly(self, connector):
@@ -321,9 +326,7 @@ def test_column_rename(self, connector: DuckDBConnector):
         connector.rename_column("test_table", "old_name", "new_name")
 
         with engine.connect() as conn:
-            result = conn.execute(
-                sa.text("SELECT * FROM test_table"),
-            )
+            result = conn.execute(sa.text("SELECT * FROM test_table"))
             assert result.keys() == ["id", "new_name"]
 
     def test_adapt_column_type(self, connector: DuckDBConnector):
@@ -341,9 +344,7 @@ def test_adapt_column_type(self, connector: DuckDBConnector):
         connector._adapt_column_type("test_table", "name", sa.types.String())
 
         with engine.connect() as conn:
-            result = conn.execute(
-                sa.text("SELECT * FROM test_table"),
-            )
+            result = conn.execute(sa.text("SELECT * FROM test_table"))
             assert result.keys() == ["id", "name"]
             assert result.cursor.description[1][1] == "STRING"
 
@@ -449,7 +450,7 @@ def test_sql_to_json_schema_map(
     assert m.to_jsonschema(sql_type) == expected_jsonschema_type
 
 
-def test_custom_type():
+def test_custom_type_to_jsonschema():
     class MyMap(SQLToJSONSchema):
         @SQLToJSONSchema.to_jsonschema.register
         def custom_number_to_jsonschema(self, column_type: sa.types.NUMERIC) -> dict:
@@ -474,3 +475,195 @@ def my_type_to_jsonschema(self, column_type) -> dict:  # noqa: ARG002
         "multipleOf": 0.01,
     }
     assert m.to_jsonschema(sa.types.BOOLEAN()) == {"type": ["boolean"]}
+
+
+class TestJSONSchemaToSQL:  # noqa: PLR0904
+    @pytest.fixture
+    def json_schema_to_sql(self) -> JSONSchemaToSQL:
+        return JSONSchemaToSQL()
+
+    def test_register_jsonschema_type_handler(
+        self,
+        json_schema_to_sql: JSONSchemaToSQL,
+    ):
+        json_schema_to_sql.register_type_handler("my-type", sa.types.LargeBinary)
+        result = json_schema_to_sql.to_sql_type({"type": "my-type"})
+        assert isinstance(result, sa.types.LargeBinary)
+
+    def test_register_jsonschema_format_handler(
+        self,
+        json_schema_to_sql: JSONSchemaToSQL,
+    ):
+        json_schema_to_sql.register_format_handler("my-format", sa.types.LargeBinary)
+        result = json_schema_to_sql.to_sql_type(
+            {
+                "type": "string",
+                "format": "my-format",
+            }
+        )
+        assert isinstance(result, sa.types.LargeBinary)
+
+    def test_string(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": ["string", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+        assert result.length is None
+
+    def test_string_max_length(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": ["string", "null"], "maxLength": 10}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(
+            json_schema_to_sql.to_sql_type(jsonschema_type),
+            sa.types.VARCHAR,
+        )
+        assert result.length == 10
+
+    def test_integer(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": ["integer", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.INTEGER)
+
+    def test_number(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": ["number", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.DECIMAL)
+
+    def test_boolean(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": ["boolean", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.BOOLEAN)
+
+    def test_object(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": "object", "properties": {}}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    def test_array(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": "array"}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    def test_array_items(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": "array", "items": {"type": "string"}}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    def test_date(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"format": "date", "type": ["string", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.DATE)
+
+    def test_time(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"format": "time", "type": ["string", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.TIME)
+
+    def test_uuid(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"format": "uuid", "type": ["string", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.UUID)
+
+    def test_datetime(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"format": "date-time", "type": ["string", "null"]}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.DATETIME)
+
+    def test_anyof_datetime(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {
+            "anyOf": [
+                {"type": "string", "format": "date-time"},
+                {"type": "null"},
+            ],
+        }
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.DATETIME)
+
+    def test_anyof_integer(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {
+            "anyOf": [
+                {"type": "null"},
+                {"type": "integer"},
+            ],
+        }
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.INTEGER)
+
+    def test_anyof_unknown(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {
+            "anyOf": [
+                {"type": "null"},
+                {"type": "unknown"},
+            ],
+        }
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    @pytest.mark.parametrize(
+        "jsonschema_type,expected_type",
+        [
+            pytest.param(
+                {"type": ["array", "object", "boolean", "null"]},
+                sa.types.VARCHAR,
+                id="array-first",
+            ),
+            pytest.param(
+                {"type": ["boolean", "array", "object", "null"]},
+                sa.types.VARCHAR,
+                id="boolean-first",
+            ),
+        ],
+    )
+    def test_complex(
+        self,
+        json_schema_to_sql: JSONSchemaToSQL,
+        jsonschema_type: dict,
+        expected_type: type[sa.types.TypeEngine],
+    ):
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, expected_type)
+
+    def test_unknown_type(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"cannot": "compute"}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    def test_unknown_format(self, json_schema_to_sql: JSONSchemaToSQL):
+        jsonschema_type = {"type": "string", "format": "unknown"}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+    def test_custom_fallback(self):
+        json_schema_to_sql = JSONSchemaToSQL()
+        json_schema_to_sql.fallback_type = sa.types.CHAR
+        jsonschema_type = {"cannot": "compute"}
+        result = json_schema_to_sql.to_sql_type(jsonschema_type)
+        assert isinstance(result, sa.types.CHAR)
+
+    def test_custom_handle_raw_string(self):
+        class CustomJSONSchemaToSQL(JSONSchemaToSQL):
+            def handle_raw_string(self, schema):
+                if schema.get("contentMediaType") == "image/png":
+                    return sa.types.LargeBinary()
+
+                return super().handle_raw_string(schema)
+
+        json_schema_to_sql = CustomJSONSchemaToSQL()
+
+        vanilla = {"type": ["string"]}
+        result = json_schema_to_sql.to_sql_type(vanilla)
+        assert isinstance(result, sa.types.VARCHAR)
+
+        non_image_type = {
+            "type": "string",
+            "contentMediaType": "text/html",
+        }
+        result = json_schema_to_sql.to_sql_type(non_image_type)
+        assert isinstance(result, sa.types.VARCHAR)
+
+        image_type = {
+            "type": "string",
+            "contentEncoding": "base64",
+            "contentMediaType": "image/png",
+        }
+        result = json_schema_to_sql.to_sql_type(image_type)
+        assert isinstance(result, sa.types.LargeBinary)
diff --git a/tests/core/test_io.py b/tests/core/test_io.py
index a48a785df..4f8b20199 100644
--- a/tests/core/test_io.py
+++ b/tests/core/test_io.py
@@ -6,6 +6,7 @@
 import io
 import itertools
 import json
+import logging
 from contextlib import nullcontext, redirect_stdout
 from textwrap import dedent
 
@@ -83,6 +84,29 @@ def test_listen_unknown_message():
         reader.listen(input_lines)
 
 
+def test_listen_error(caplog: pytest.LogCaptureFixture):
+    class ErrorReader(DummyReader):
+        def _process_record_message(self, message_dict: dict) -> None:  # noqa: ARG002
+            msg = "Bad record"
+            raise ValueError(msg)
+
+    message = RecordMessage(
+        stream="users",
+        record={"id": 1, "value": 1.23},
+    )
+
+    input_lines = io.StringIO(json.dumps(message.to_dict()) + "\n")
+
+    reader = ErrorReader()
+    with caplog.at_level(logging.DEBUG), pytest.raises(ValueError, match="Bad record"):
+        reader.listen(input_lines)
+
+    assert caplog.records
+
+    message = caplog.records[0].message
+    assert "Failed while processing Singer message" in message
+
+
 def test_write_message():
     writer = SingerWriter()
     message = RecordMessage(
diff --git a/tests/core/test_jsonschema_helpers.py b/tests/core/test_jsonschema_helpers.py
index aeb2bae0b..488030392 100644
--- a/tests/core/test_jsonschema_helpers.py
+++ b/tests/core/test_jsonschema_helpers.py
@@ -252,6 +252,17 @@ def test_property_description():
     }
 
 
+def test_property_title():
+    title = "My Test Property"
+    prop = Property("test_property", StringType, title=title)
+    assert prop.to_dict() == {
+        "test_property": {
+            "type": ["string", "null"],
+            "title": title,
+        },
+    }
+
+
 @pytest.mark.parametrize(
     "json_type,expected_json_schema",
     [
diff --git a/tests/core/test_mapper.py b/tests/core/test_mapper.py
index a776689a1..0ade78823 100644
--- a/tests/core/test_mapper.py
+++ b/tests/core/test_mapper.py
@@ -23,6 +23,7 @@
     ArrayType,
     BooleanType,
     CustomType,
+    DateTimeType,
     IntegerType,
     NumberType,
     ObjectType,
@@ -626,6 +627,7 @@ class MappedStream(Stream):
                 Property("some_numbers", ArrayType(NumberType())),
             ),
         ),
+        Property("joined_at", DateTimeType),
     ).to_dict()
 
     def get_records(self, context):  # noqa: ARG002
@@ -637,6 +639,7 @@ def get_records(self, context):  # noqa: ARG002
                 "sub": {"num": 1, "custom_obj": CustomObj("hello")},
                 "some_numbers": [Decimal("3.14"), Decimal("2.718")],
             },
+            "joined_at": "2022-01-01T00:00:00Z",
         }
         yield {
             "email": "bob@example.com",
@@ -646,6 +649,7 @@ def get_records(self, context):  # noqa: ARG002
                 "sub": {"num": 2, "custom_obj": CustomObj("world")},
                 "some_numbers": [Decimal("10.32"), Decimal("1.618")],
             },
+            "joined_at": "2022-01-01T00:00:00Z",
         }
         yield {
             "email": "charlie@example.com",
@@ -655,6 +659,7 @@ def get_records(self, context):  # noqa: ARG002
                 "sub": {"num": 3, "custom_obj": CustomObj("hello")},
                 "some_numbers": [Decimal("1.414"), Decimal("1.732")],
             },
+            "joined_at": "2022-01-01T00:00:00Z",
         }
 
     def get_batches(self, batch_config, context):  # noqa: ARG002
@@ -768,6 +773,58 @@ def discover_streams(self):
             "aliased_stream_batch.jsonl",
             id="aliased_stream_batch",
         ),
+        pytest.param(
+            {"mystream": {"__alias__": "aliased.stream"}},
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "aliased_stream_not_expr.jsonl",
+            id="aliased_stream_not_expr",
+        ),
+        pytest.param(
+            {"mystream": {"__alias__": "'__stream_name__'"}},
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "aliased_stream_quoted.jsonl",
+            id="aliased_stream_quoted",
+        ),
+        pytest.param(
+            {"mystream": {"source_table": "__stream_name__"}},
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "builtin_variable_stream_name.jsonl",
+            id="builtin_variable_stream_name",
+        ),
+        pytest.param(
+            {"mystream": {"__alias__": "'aliased_' + __stream_name__"}},
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "builtin_variable_stream_name_alias.jsonl",
+            id="builtin_variable_stream_name_alias",
+        ),
+        pytest.param(
+            {"mystream": {"__alias__": "__stream_name__.upper()"}},
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "builtin_variable_stream_name_alias_expr.jsonl",
+            id="builtin_variable_stream_name_alias_expr",
+        ),
+        pytest.param(
+            {
+                "mystream": {
+                    "email": "self.upper()",
+                    "__else__": None,
+                }
+            },
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "builtin_variable_self.jsonl",
+            id="builtin_variable_self",
+        ),
+        pytest.param(
+            {
+                "mystream": {
+                    "email": "_['email'].upper()",
+                    "__else__": None,
+                }
+            },
+            {"flattening_enabled": False, "flattening_max_depth": 0},
+            "builtin_variable_underscore.jsonl",
+            id="builtin_variable_underscore",
+        ),
         pytest.param(
             {},
             {"flattening_enabled": True, "flattening_max_depth": 0},
@@ -890,6 +947,22 @@ def discover_streams(self):
             "fake_email_seed_instance.jsonl",
             id="fake_email_seed_instance",
         ),
+        pytest.param(
+            {
+                "mystream": {
+                    "joined_date": "datetime.datetime.fromisoformat(joined_at).date()",
+                    "joined_timestamp": "float(datetime.datetime.fromisoformat(joined_at).timestamp())",  # noqa: E501
+                    "some_datetime": "datetime.datetime.fromisoformat(config['some_date_string'])",  # noqa: E501
+                },
+            },
+            {
+                "stream_map_config": {
+                    "some_date_string": "2024-10-10T10:10:10Z",
+                },
+            },
+            "dates.jsonl",
+            id="dates",
+        ),
     ],
 )
 def test_mapped_stream(
diff --git a/tests/core/test_sql_typing.py b/tests/core/test_sql_typing.py
index 5662d7d0d..8b6ff1a96 100644
--- a/tests/core/test_sql_typing.py
+++ b/tests/core/test_sql_typing.py
@@ -49,7 +49,8 @@ def test_convert_jsonschema_type_to_sql_type(
     jsonschema_type: dict,
     sql_type: sa.types.TypeEngine,
 ):
-    result = th.to_sql_type(jsonschema_type)
+    with pytest.warns(DeprecationWarning):
+        result = th.to_sql_type(jsonschema_type)
     assert isinstance(result, sql_type.__class__)
     assert str(result) == str(sql_type)
 
diff --git a/tests/core/test_state_handling.py b/tests/core/test_state_handling.py
index f58a0128b..85fd4812f 100644
--- a/tests/core/test_state_handling.py
+++ b/tests/core/test_state_handling.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import logging
+import uuid
 
 import pytest
 
@@ -155,3 +156,21 @@ def test_null_replication_value(caplog):
     ), "State should not be updated."
     assert caplog.records[0].levelname == "WARNING"
     assert "is null" in caplog.records[0].message
+
+
+def test_uuidv7_replication_value():
+    stream_state = {
+        "replication_key": "id",
+        "replication_key_value": "01931c63-b14e-7ff3-8621-e577ed392dc8",
+    }
+    new_string_val = "01931c63-b14e-7ff3-8621-e578edbca9a3"
+
+    _state.increment_state(
+        stream_state,
+        latest_record={"id": uuid.UUID(new_string_val)},
+        replication_key="id",
+        is_sorted=True,
+        check_sorted=True,
+    )
+
+    assert stream_state["replication_key_value"] == new_string_val
diff --git a/tests/core/test_streams.py b/tests/core/test_streams.py
index 1a25defac..038f87657 100644
--- a/tests/core/test_streams.py
+++ b/tests/core/test_streams.py
@@ -5,6 +5,7 @@
 import datetime
 import logging
 import typing as t
+import urllib.parse
 
 import pytest
 import requests
@@ -15,8 +16,7 @@
 )
 from singer_sdk.helpers._classproperty import classproperty
 from singer_sdk.helpers._compat import datetime_fromisoformat as parse
-from singer_sdk.helpers.jsonpath import _compile_jsonpath, extract_jsonpath
-from singer_sdk.pagination import first
+from singer_sdk.helpers.jsonpath import _compile_jsonpath
 from singer_sdk.streams.core import REPLICATION_FULL_TABLE, REPLICATION_INCREMENTAL
 from singer_sdk.streams.graphql import GraphQLStream
 from singer_sdk.streams.rest import RESTStream
@@ -24,6 +24,8 @@
 from tests.core.conftest import SimpleTestStream
 
 if t.TYPE_CHECKING:
+    import requests_mock
+
     from singer_sdk import Stream, Tap
     from tests.core.conftest import SimpleTestTap
 
@@ -42,22 +44,16 @@ class RestTestStream(RESTStream):
     ).to_dict()
     replication_key = "updatedAt"
 
+
+class RestTestStreamLegacyPagination(RestTestStream):
+    """Test RESTful stream class with pagination."""
+
     def get_next_page_token(
         self,
-        response: requests.Response,
-        previous_token: str | None,  # noqa: ARG002
-    ) -> str | None:
-        if not self.next_page_token_jsonpath:
-            return response.headers.get("X-Next-Page", None)
-
-        all_matches = extract_jsonpath(
-            self.next_page_token_jsonpath,
-            response.json(),
-        )
-        try:
-            return first(all_matches)
-        except StopIteration:
-            return None
+        response: requests.Response,  # noqa: ARG002
+        previous_token: int | None,
+    ) -> int:
+        return previous_token + 1 if previous_token is not None else 1
 
 
 class GraphqlTestStream(GraphQLStream):
@@ -316,6 +312,21 @@ def test_jsonpath_rest_stream(tap: Tap, path: str, content: str, result: list[di
     assert list(records) == result
 
 
+def test_legacy_pagination(tap: Tap):
+    """Validate legacy pagination is handled correctly."""
+    stream = RestTestStreamLegacyPagination(tap)
+
+    with pytest.deprecated_call():
+        stream.get_new_paginator()
+
+    page: int | None = None
+    page = stream.get_next_page_token(None, page)
+    assert page == 1
+
+    page = stream.get_next_page_token(None, page)
+    assert page == 2
+
+
 def test_jsonpath_graphql_stream_default(tap: Tap):
     """Validate graphql JSONPath, defaults to the stream name."""
     content = """{
@@ -437,11 +448,8 @@ def test_next_page_token_jsonpath(
     RestTestStream.next_page_token_jsonpath = path
     stream = RestTestStream(tap)
 
-    with pytest.warns(DeprecationWarning):
-        paginator = stream.get_new_paginator()
-
+    paginator = stream.get_new_paginator()
     next_page = paginator.get_next(fake_response)
-
     assert next_page == result
 
 
@@ -484,6 +492,45 @@ def calculate_test_cost(
         assert f"Total Sync costs for stream {stream.name}" in record.message
 
 
+def test_non_json_payload(tap: Tap, requests_mock: requests_mock.Mocker):
+    """Test non-JSON payload is handled correctly."""
+
+    def callback(request: requests.PreparedRequest, context: requests_mock.Context):  # noqa: ARG001
+        assert request.headers["Content-Type"] == "application/x-www-form-urlencoded"
+        assert request.body == "my_key=my_value"
+
+        data = urllib.parse.parse_qs(request.body)
+
+        return {
+            "data": [
+                {"id": 1, "value": f"{data['my_key'][0]}_1"},
+                {"id": 2, "value": f"{data['my_key'][0]}_2"},
+            ]
+        }
+
+    class NonJsonStream(RestTestStream):
+        payload_as_json = False
+        http_method = "POST"
+        path = "/non-json"
+        records_jsonpath = "$.data[*]"
+
+        def prepare_request_payload(self, context, next_page_token):  # noqa: ARG002
+            return {"my_key": "my_value"}
+
+    stream = NonJsonStream(tap)
+
+    requests_mock.post(
+        "https://example.com/non-json",
+        json=callback,
+    )
+
+    records = list(stream.request_records(None))
+    assert records == [
+        {"id": 1, "value": "my_value_1"},
+        {"id": 2, "value": "my_value_2"},
+    ]
+
+
 @pytest.mark.parametrize(
     "input_catalog,selection",
     [
diff --git a/tests/core/test_typing.py b/tests/core/test_typing.py
index 5043c75e1..c6919a81d 100644
--- a/tests/core/test_typing.py
+++ b/tests/core/test_typing.py
@@ -313,9 +313,19 @@ def test_conform_primitives():
 
     assert _conform_primitive_property(None, {"type": "boolean"}) is None
     assert _conform_primitive_property(0, {"type": "boolean"}) is False
+    assert (
+        _conform_primitive_property(
+            0, {"anyOf": [{"type": "boolean"}, {"type": "integer"}]}
+        )
+        == 0
+    )
+    assert _conform_primitive_property(0, {"type": ["boolean", "integer"]}) == 0
     assert _conform_primitive_property(1, {"type": "boolean"}) is True
+    assert _conform_primitive_property(1, {"type": ["boolean", "null"]}) is True
+    assert _conform_primitive_property(1, {"type": ["boolean"]}) is True
 
 
+@pytest.mark.filterwarnings("ignore:Use `JSONSchemaToSQL` instead.:DeprecationWarning")
 @pytest.mark.parametrize(
     "jsonschema_type,expected",
     [
@@ -336,6 +346,10 @@ def test_conform_primitives():
             sa.types.DATETIME,
         ),
         ({"anyOf": [{"type": "integer"}, {"type": "null"}]}, sa.types.INTEGER),
+        (
+            {"type": ["array", "object", "boolean", "null"]},
+            sa.types.VARCHAR,
+        ),
     ],
 )
 def test_to_sql_type(jsonschema_type, expected):
diff --git a/tests/samples/test_target_csv.py b/tests/samples/test_target_csv.py
index 3053590d8..7ada6c33f 100644
--- a/tests/samples/test_target_csv.py
+++ b/tests/samples/test_target_csv.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import datetime
+import importlib.resources
 import json
 import shutil
 import typing as t
@@ -16,7 +17,6 @@
 from samples.sample_mapper.mapper import StreamTransform
 from samples.sample_tap_countries.countries_tap import SampleTapCountries
 from samples.sample_target_csv.csv_target import SampleTargetCSV
-from singer_sdk.helpers._compat import importlib_resources
 from singer_sdk.testing import (
     get_target_test_class,
     sync_end_to_end,
@@ -149,7 +149,7 @@ def test_target_batching():
 
 
 SAMPLE_FILENAME = (
-    importlib_resources.files("tests.samples") / "resources/messages.jsonl"
+    importlib.resources.files("tests.samples") / "resources/messages.jsonl"
 )
 EXPECTED_OUTPUT = """"id"	"name"
 1	"Chris"
diff --git a/tests/snapshots/mapped_stream/aliased_stream.jsonl b/tests/snapshots/mapped_stream/aliased_stream.jsonl
index 31534b633..d4c4cc942 100644
--- a/tests/snapshots/mapped_stream/aliased_stream.jsonl
+++ b/tests/snapshots/mapped_stream/aliased_stream.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"aliased_stream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]}},"type":"object","required":["email"]},"key_properties":[]}
-{"type":"RECORD","stream":"aliased_stream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"aliased_stream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"aliased_stream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"SCHEMA","stream":"aliased_stream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"aliased_stream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"aliased_stream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"aliased_stream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/aliased_stream_batch.jsonl b/tests/snapshots/mapped_stream/aliased_stream_batch.jsonl
index c28e8b9e2..6b0dbe121 100644
--- a/tests/snapshots/mapped_stream/aliased_stream_batch.jsonl
+++ b/tests/snapshots/mapped_stream/aliased_stream_batch.jsonl
@@ -1,5 +1,5 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"aliased_stream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"SCHEMA","stream":"aliased_stream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
 {"type":"BATCH","stream":"aliased_stream","encoding":{"format":"jsonl","compression":"gzip"},"manifest":["file:///tmp/stream.json.gz"]}
 {"type":"STATE","value":{}}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/aliased_stream_not_expr.jsonl b/tests/snapshots/mapped_stream/aliased_stream_not_expr.jsonl
new file mode 100644
index 000000000..8a341c09f
--- /dev/null
+++ b/tests/snapshots/mapped_stream/aliased_stream_not_expr.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"aliased.stream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"aliased.stream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"aliased.stream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"aliased.stream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/aliased_stream_quoted.jsonl b/tests/snapshots/mapped_stream/aliased_stream_quoted.jsonl
new file mode 100644
index 000000000..bd3f0cb04
--- /dev/null
+++ b/tests/snapshots/mapped_stream/aliased_stream_quoted.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"__stream_name__","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"__stream_name__","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"__stream_name__","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"__stream_name__","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/builtin_variable_self.jsonl b/tests/snapshots/mapped_stream/builtin_variable_self.jsonl
new file mode 100644
index 000000000..4711ac95a
--- /dev/null
+++ b/tests/snapshots/mapped_stream/builtin_variable_self.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"mystream","schema":{"type":"object","properties":{"email":{"type":["string","null"]}}},"key_properties":[]}
+{"type":"RECORD","stream":"mystream","record":{"email":"ALICE@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"BOB@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"CHARLIE@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/builtin_variable_stream_name.jsonl b/tests/snapshots/mapped_stream/builtin_variable_stream_name.jsonl
new file mode 100644
index 000000000..3fd81e87a
--- /dev/null
+++ b/tests/snapshots/mapped_stream/builtin_variable_stream_name.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]},"source_table":{"type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
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+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias.jsonl b/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias.jsonl
new file mode 100644
index 000000000..8c56822cd
--- /dev/null
+++ b/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"aliased_mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
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+{"type":"RECORD","stream":"aliased_mystream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"aliased_mystream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias_expr.jsonl b/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias_expr.jsonl
new file mode 100644
index 000000000..8b4257369
--- /dev/null
+++ b/tests/snapshots/mapped_stream/builtin_variable_stream_name_alias_expr.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"MYSTREAM","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"MYSTREAM","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"MYSTREAM","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"MYSTREAM","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/builtin_variable_underscore.jsonl b/tests/snapshots/mapped_stream/builtin_variable_underscore.jsonl
new file mode 100644
index 000000000..4711ac95a
--- /dev/null
+++ b/tests/snapshots/mapped_stream/builtin_variable_underscore.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"mystream","schema":{"type":"object","properties":{"email":{"type":["string","null"]}}},"key_properties":[]}
+{"type":"RECORD","stream":"mystream","record":{"email":"ALICE@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"BOB@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"CHARLIE@EXAMPLE.COM"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/dates.jsonl b/tests/snapshots/mapped_stream/dates.jsonl
new file mode 100644
index 000000000..43ae073ec
--- /dev/null
+++ b/tests/snapshots/mapped_stream/dates.jsonl
@@ -0,0 +1,6 @@
+{"type":"STATE","value":{}}
+{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]},"joined_date":{"type":["string","null"],"format":"date"},"joined_timestamp":{"type":["number","null"]},"some_datetime":{"type":["string","null"],"format":"date-time"}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z","joined_date":"2022-01-01","joined_timestamp":1640995200.0,"some_datetime":"2024-10-10T10:10:10+00:00"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z","joined_date":"2022-01-01","joined_timestamp":1640995200.0,"some_datetime":"2024-10-10T10:10:10+00:00"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z","joined_date":"2022-01-01","joined_timestamp":1640995200.0,"some_datetime":"2024-10-10T10:10:10+00:00"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/drop_property.jsonl b/tests/snapshots/mapped_stream/drop_property.jsonl
index f9d032b74..84bfa899d 100644
--- a/tests/snapshots/mapped_stream/drop_property.jsonl
+++ b/tests/snapshots/mapped_stream/drop_property.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]}},"type":"object","required":[]},"key_properties":[]}
-{"type":"RECORD","stream":"mystream","record":{"count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":[]},"key_properties":[]}
+{"type":"RECORD","stream":"mystream","record":{"count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/drop_property_null_string.jsonl b/tests/snapshots/mapped_stream/drop_property_null_string.jsonl
index f9d032b74..84bfa899d 100644
--- a/tests/snapshots/mapped_stream/drop_property_null_string.jsonl
+++ b/tests/snapshots/mapped_stream/drop_property_null_string.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]}},"type":"object","required":[]},"key_properties":[]}
-{"type":"RECORD","stream":"mystream","record":{"count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
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+{"type":"RECORD","stream":"mystream","record":{"count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/flatten_all.jsonl b/tests/snapshots/mapped_stream/flatten_all.jsonl
index cb0a6d157..cdc5ddd99 100644
--- a/tests/snapshots/mapped_stream/flatten_all.jsonl
+++ b/tests/snapshots/mapped_stream/flatten_all.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user__id":{"type":["integer","null"]},"user__sub__num":{"type":["integer","null"]},"user__sub__custom_obj":{"type":["string","null"]},"user__some_numbers":{"type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
-{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user__id":1,"user__sub__num":1,"user__sub__custom_obj":"obj-hello","user__some_numbers":"[3.14,2.718]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user__id":2,"user__sub__num":2,"user__sub__custom_obj":"obj-world","user__some_numbers":"[10.32,1.618]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user__id":3,"user__sub__num":3,"user__sub__custom_obj":"obj-hello","user__some_numbers":"[1.414,1.732]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
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+{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user__id":1,"user__sub__num":1,"user__sub__custom_obj":"obj-hello","user__some_numbers":"[3.14,2.718]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user__id":2,"user__sub__num":2,"user__sub__custom_obj":"obj-world","user__some_numbers":"[10.32,1.618]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user__id":3,"user__sub__num":3,"user__sub__custom_obj":"obj-hello","user__some_numbers":"[1.414,1.732]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/flatten_depth_0.jsonl b/tests/snapshots/mapped_stream/flatten_depth_0.jsonl
index 3b7964a4c..99ecd5c17 100644
--- a/tests/snapshots/mapped_stream/flatten_depth_0.jsonl
+++ b/tests/snapshots/mapped_stream/flatten_depth_0.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user":{"properties":{"id":{"type":["integer","null"]},"sub":{"properties":{"num":{"type":["integer","null"]},"custom_obj":{"type":["string","null"]}},"type":["object","null"]},"some_numbers":{"items":{"type":["number"]},"type":["array","null"]}},"type":["object","null"]}},"type":"object","required":["email"]},"key_properties":[]}
-{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]}},"time_extracted":"2022-01-01T00:00:00+00:00"}
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+{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user":{"id":1,"sub":{"num":1,"custom_obj":"obj-hello"},"some_numbers":[3.14,2.718]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user":{"id":2,"sub":{"num":2,"custom_obj":"obj-world"},"some_numbers":[10.32,1.618]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user":{"id":3,"sub":{"num":3,"custom_obj":"obj-hello"},"some_numbers":[1.414,1.732]},"joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/flatten_depth_1.jsonl b/tests/snapshots/mapped_stream/flatten_depth_1.jsonl
index d289099b9..f3d54bfb0 100644
--- a/tests/snapshots/mapped_stream/flatten_depth_1.jsonl
+++ b/tests/snapshots/mapped_stream/flatten_depth_1.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
-{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user__id":{"type":["integer","null"]},"user__sub":{"type":["string","null"]},"user__some_numbers":{"type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
-{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user__id":1,"user__sub":"{\"num\":1,\"custom_obj\":\"obj-hello\"}","user__some_numbers":"[3.14,2.718]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user__id":2,"user__sub":"{\"num\":2,\"custom_obj\":\"obj-world\"}","user__some_numbers":"[10.32,1.618]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
-{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user__id":3,"user__sub":"{\"num\":3,\"custom_obj\":\"obj-hello\"}","user__some_numbers":"[1.414,1.732]"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"SCHEMA","stream":"mystream","schema":{"properties":{"email":{"type":["string"]},"count":{"type":["integer","null"]},"user__id":{"type":["integer","null"]},"user__sub":{"type":["string","null"]},"user__some_numbers":{"type":["string","null"]},"joined_at":{"format":"date-time","type":["string","null"]}},"type":"object","required":["email"]},"key_properties":[]}
+{"type":"RECORD","stream":"mystream","record":{"email":"alice@example.com","count":21,"user__id":1,"user__sub":"{\"num\":1,\"custom_obj\":\"obj-hello\"}","user__some_numbers":"[3.14,2.718]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"bob@example.com","count":13,"user__id":2,"user__sub":"{\"num\":2,\"custom_obj\":\"obj-world\"}","user__some_numbers":"[10.32,1.618]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
+{"type":"RECORD","stream":"mystream","record":{"email":"charlie@example.com","count":19,"user__id":3,"user__sub":"{\"num\":3,\"custom_obj\":\"obj-hello\"}","user__some_numbers":"[1.414,1.732]","joined_at":"2022-01-01T00:00:00Z"},"time_extracted":"2022-01-01T00:00:00+00:00"}
 {"type":"STATE","value":{"bookmarks":{"mystream":{}}}}
diff --git a/tests/snapshots/mapped_stream/keep_all_fields.jsonl b/tests/snapshots/mapped_stream/keep_all_fields.jsonl
index 4b6ffcfb2..9176918f2 100644
--- a/tests/snapshots/mapped_stream/keep_all_fields.jsonl
+++ b/tests/snapshots/mapped_stream/keep_all_fields.jsonl
@@ -1,6 +1,6 @@
 {"type":"STATE","value":{}}
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diff --git a/tests/snapshots/mapped_stream/map_and_flatten.jsonl b/tests/snapshots/mapped_stream/map_and_flatten.jsonl
index 06e1576b9..df06b7f1f 100644
--- a/tests/snapshots/mapped_stream/map_and_flatten.jsonl
+++ b/tests/snapshots/mapped_stream/map_and_flatten.jsonl
@@ -1,6 +1,6 @@
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diff --git a/tests/snapshots/mapped_stream/no_map.jsonl b/tests/snapshots/mapped_stream/no_map.jsonl
index 3b7964a4c..99ecd5c17 100644
--- a/tests/snapshots/mapped_stream/no_map.jsonl
+++ b/tests/snapshots/mapped_stream/no_map.jsonl
@@ -1,6 +1,6 @@
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diff --git a/tests/snapshots/mapped_stream/record_to_column.jsonl b/tests/snapshots/mapped_stream/record_to_column.jsonl
index 3ee82a85f..9a2c450ba 100644
--- a/tests/snapshots/mapped_stream/record_to_column.jsonl
+++ b/tests/snapshots/mapped_stream/record_to_column.jsonl
@@ -1,6 +1,6 @@
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diff --git a/tests/snapshots/mapped_stream/sourced_stream_1.jsonl b/tests/snapshots/mapped_stream/sourced_stream_1.jsonl
index 9e841394b..753e15da4 100644
--- a/tests/snapshots/mapped_stream/sourced_stream_1.jsonl
+++ b/tests/snapshots/mapped_stream/sourced_stream_1.jsonl
@@ -1,6 +1,6 @@
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diff --git a/tests/snapshots/mapped_stream/sourced_stream_1_null_string.jsonl b/tests/snapshots/mapped_stream/sourced_stream_1_null_string.jsonl
index 9e841394b..753e15da4 100644
--- a/tests/snapshots/mapped_stream/sourced_stream_1_null_string.jsonl
+++ b/tests/snapshots/mapped_stream/sourced_stream_1_null_string.jsonl
@@ -1,6 +1,6 @@
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diff --git a/tests/snapshots/mapped_stream/sourced_stream_2.jsonl b/tests/snapshots/mapped_stream/sourced_stream_2.jsonl
index 7d9efc5e2..c677521cf 100644
--- a/tests/snapshots/mapped_stream/sourced_stream_2.jsonl
+++ b/tests/snapshots/mapped_stream/sourced_stream_2.jsonl
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