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SMTP.SendEmail - Added AcceptAllCerts parameter #26

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@RikuVirtanen RikuVirtanen commented Nov 20, 2024

#25

[1.3.0] - 2024-09-30

Added

  • [Breaking] Added parameter AcceptAllCerts which will make the Task to accept all server certifications.

Summary by CodeRabbit

Release Notes for Frends.SMTP.SendEmail Version 1.3.0

  • New Features

    • Introduced AcceptAllCerts parameter to allow acceptance of all server certificates during email sending.
    • Enhanced support for secure socket options and certificate handling.
  • Bug Fixes

    • Improved connection handling for SMTP servers without authentication.
  • Tests

    • Added new test methods to validate email sending functionality with the new AcceptAllCerts option.
    • Expanded test coverage for secure connections and certificate validation.
  • Documentation

    • Updated changelog to reflect new version details and changes.

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coderabbitai bot commented Nov 20, 2024

Walkthrough

The pull request introduces several changes to the Frends.SMTP.SendEmail module, notably updating it to version 1.3.0. This version adds a breaking change with the new AcceptAllCerts parameter, allowing acceptance of all server certificates. The project structure has been updated to include the Moq package for testing enhancements. Additionally, new test methods have been created to validate email sending functionality, especially regarding secure connections and certificate handling. The internal visibility of certain members has been improved for better testability.

Changes

File Path Change Summary
Frends.SMTP.SendEmail/CHANGELOG.md Updated changelog for version 1.3.0; added AcceptAllCerts parameter; noted previous version changes.
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/Frends.Smtp.Tests.csproj Added package reference for Moq version 4.20.72.
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs Added AcceptAllCerts property; introduced new test methods for secure socket options and certificate handling.
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs Added public bool AcceptAllCerts { get; set; } property to Options class.
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Frends.Smtp.SendEmail.csproj Updated version to 1.3.0; added InternalsVisibleTo attribute for testing.
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs Modified InitializeSmtpClient method for internal access and added optional SmtpClient parameter; updated logic for certificate handling.

Sequence Diagram(s)

sequenceDiagram
    participant User
    participant SendEmailTask
    participant SmtpClient

    User->>SendEmailTask: Send email request with AcceptAllCerts
    SendEmailTask->>SmtpClient: Initialize SMTP client
    alt AcceptAllCerts is true
        SmtpClient->>SmtpClient: Set certificate validation to accept all
    end
    SendEmailTask->>SmtpClient: Send email
    SmtpClient-->>User: Email sent confirmation
Loading

🐰 "In the land of code, where emails fly,
A new parameter lets us try,
With certificates all accepted,
Our emails now are well-protected!
So hop along, let's test away,
With Moq and joy, we code and play!" 🐇


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📒 Files selected for processing (1)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (3 hunks)
🚧 Files skipped from review as they are similar to previous changes (1)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs

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Actionable comments posted: 3

🧹 Outside diff range and nitpick comments (1)
Frends.SMTP.SendEmail/CHANGELOG.md (1)

5-5: Improve parameter description clarity

The current description "which will make the Task to accept all server certifications" could be more precise.

- - [Breaking] Added parameter AcceptAllCerts which will make the Task to accept all server certifications.
+ - [Breaking] Added parameter AcceptAllCerts which allows the Task to accept SMTP servers with untrusted or self-signed SSL/TLS certificates.
📜 Review details

Configuration used: CodeRabbit UI
Review profile: CHILL

📥 Commits

Reviewing files that changed from the base of the PR and between d86949b and bcc45c2.

📒 Files selected for processing (6)
  • Frends.SMTP.SendEmail/CHANGELOG.md (1 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/Frends.Smtp.Tests.csproj (1 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (4 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs (1 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Frends.Smtp.SendEmail.csproj (2 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (4 hunks)
🧰 Additional context used
🪛 GitHub Check: build / Build on windows-latest
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs

[failure] 147-147:
Syntax error; value expected


[failure] 147-147:
; expected


[failure] 147-147:
} expected


[failure] 150-150:
Syntax error; value expected


[failure] 150-150:
; expected


[failure] 150-150:
} expected


[failure] 153-153:
Syntax error; value expected


[failure] 153-153:
; expected


[failure] 153-153:
} expected


[failure] 147-147:
Syntax error; value expected

🔇 Additional comments (12)
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/Frends.Smtp.Tests.csproj (2)

21-21: LGTM! Moq package addition is appropriate for testing the new AcceptAllCerts feature.

The addition of Moq 4.20.72 will enable proper isolation testing of the SMTP client behavior, particularly for scenarios involving certificate validation.


21-21: Ensure comprehensive testing of certificate validation scenarios.

Given that this PR introduces certificate validation bypass functionality, please ensure the test coverage includes:

  • Default secure behavior (certificate validation enabled)
  • Certificate bypass scenarios
  • Error cases and edge conditions
  • Security implications of AcceptAllCerts usage
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Frends.Smtp.SendEmail.csproj (3)

5-5: LGTM: Version bump follows semantic versioning

The version increase from 1.2.1 to 1.3.0 appropriately reflects the breaking change introduced by the AcceptAllCerts parameter.


35-39: LGTM: Test visibility properly configured

The InternalsVisibleTo attribute is correctly implemented using the MSBuild project name, enabling proper unit testing of internal components.


Line range hint 1-40: Consider security documentation for AcceptAllCerts feature

Given that this PR introduces a feature to bypass certificate validation (AcceptAllCerts), consider:

  1. Adding XML documentation comments to clearly warn about security implications
  2. Updating the README.md with security best practices
  3. Adding a warning in the task's UI when this option is enabled

This will help users understand the security trade-offs of accepting all certificates.

Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs (1)

33-38: ⚠️ Potential issue

Fix incorrect server type in documentation and add security warnings

The XML documentation has a few issues:

  1. It incorrectly mentions "IMAP server" instead of "SMTP server"
  2. It lacks important security warnings about the risks of accepting invalid certificates

Apply this diff to improve the documentation:

     /// <summary>
-    /// Should the task accept all certificates from IMAP server, including invalid ones?
+    /// Should the task accept all certificates from SMTP server, including invalid ones?
+    /// WARNING: Enabling this option bypasses certificate validation and poses significant security risks.
+    /// It should only be used in controlled environments where self-signed certificates are necessary.
+    /// Using this in production environments could expose the system to man-in-the-middle attacks.
     /// </summary>

Additionally, this change is marked as breaking in the PR description, but adding a new property with a false default value shouldn't break existing functionality. Consider revising the breaking change classification.

Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (3)

2-2: LGTM! Setup changes look good.

The new imports and default configuration are appropriate for the new functionality. Good security practice setting AcceptAllCerts = false by default.

Also applies to: 7-10, 83-84


Line range hint 1-248: Security Advisory: Document risks of AcceptAllCerts

Given that this PR introduces the ability to bypass certificate validation, please ensure:

  1. Add clear documentation about the security implications of enabling AcceptAllCerts
  2. Add warnings in the README and API documentation
  3. Consider logging a warning when this option is enabled
  4. Consider adding this setting to security scanning/audit tools

106-117: 🛠️ Refactor suggestion

Enhance test coverage for AcceptAllCerts feature.

While this test verifies basic functionality, consider adding:

  1. Negative test cases (e.g., with invalid certificates)
  2. Verification that certificates are actually being bypassed
  3. Test cases with different SecureSocket options
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (3)

101-101: Access modifier change to internal approved for testing purposes

Changing InitializeSmtpClient from private to internal allows the test assembly to access this method, facilitating unit testing.


103-103: Initialization of SmtpClient with null-coalescing assignment

The use of client ??= new SmtpClient(); correctly initializes the client if it's null.


105-111: ⚠️ Potential issue

Use caution with AcceptAllCerts option due to security risks

Setting ServerCertificateValidationCallback to always return true disables SSL/TLS certificate validation, which poses significant security risks such as man-in-the-middle attacks. Ensure that the AcceptAllCerts option is used only in secure, controlled environments. Consider adding documentation and warnings to inform users of the potential risks.

Frends.SMTP.SendEmail/CHANGELOG.md Outdated Show resolved Hide resolved
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Actionable comments posted: 1

🧹 Outside diff range and nitpick comments (3)
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (3)

101-103: Document breaking changes in XML comments

The method signature has changed significantly. Consider adding XML documentation to explain:

  • The purpose of the optional client parameter
  • The change from 'settings' to 'options' parameter name

126-131: Add input validation for authentication parameters

The authentication mechanism selection looks good, but consider adding validation:

 if (options.UseOAuth2)
+{
+    if (string.IsNullOrEmpty(options.Token))
+        throw new ArgumentException("OAuth2 token is required when UseOAuth2 is true");
     mechanism = new SaslMechanismOAuth2(options.UserName, options.Token);
+}
 else if (string.IsNullOrEmpty(options.Password))
     return client;
 else
+{
+    if (string.IsNullOrEmpty(options.UserName))
+        throw new ArgumentException("Username is required for basic authentication");
     mechanism = new SaslMechanismLogin(new NetworkCredential(options.UserName, options.Password));
+}

Line range hint 101-122: Consider alternative approaches to certificate handling

Instead of a boolean AcceptAllCerts option, consider these more secure alternatives:

  1. Certificate thumbprint validation:

    • Allow specifying expected certificate thumbprints
    • Validate against the list instead of accepting all
  2. Custom certificate validation:

    • Add a callback parameter for custom validation logic
    • Enable more granular control over certificate acceptance
  3. Certificate path configuration:

    • Allow specifying trusted certificate paths
    • Use system certificate store integration

This would provide better security while maintaining flexibility for self-signed certificates.

📜 Review details

Configuration used: CodeRabbit UI
Review profile: CHILL

📥 Commits

Reviewing files that changed from the base of the PR and between bcc45c2 and 49f0b34.

📒 Files selected for processing (1)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (3 hunks)
🔇 Additional comments (1)
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (1)

15-15: LGTM: Test visibility changes are appropriate

The addition of InternalsVisibleTo attribute is a good practice for enabling proper unit testing while maintaining encapsulation.

Also applies to: 17-17

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Actionable comments posted: 1

🧹 Outside diff range and nitpick comments (4)
Frends.SMTP.SendEmail/CHANGELOG.md (2)

6-8: Consider adding certificate management alternatives

While the current documentation clearly warns about security risks, it would be helpful to add information about proper certificate management alternatives, such as:

  • How to properly install and trust certificates
  • Where to obtain valid certificates
  • Links to documentation about proper certificate management
🧰 Tools
🪛 Markdownlint

7-7: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


8-8: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


6-6: Expected: 2; Actual: 1
Unordered list indentation

(MD007, ul-indent)


7-7: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


8-8: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


6-6: Column: 1
Hard tabs

(MD010, no-hard-tabs)


6-8: Fix markdown formatting inconsistencies

There are several markdown formatting issues that should be addressed:

  • Inconsistent list indentation (should be 2 spaces)
  • Usage of hard tabs (should be spaces)

Apply this formatting fix:

-## [1.3.0] - 2024-09-30
-### Added
-- [Breaking] Added parameter AcceptAllCerts which allows bypassing SSL/TLS certificate validation for SMTP servers.
-	- Default value: false
-    - Warning: Enabling this option poses security risks. Only use when connecting to trusted SMTP servers with self-signed certificates.
-    - Usage: Enable only in controlled environments where certificate validation issues cannot be resolved through proper certificate installation.
+## [1.3.0] - 2024-09-30
+### Added
+- [Breaking] Added parameter AcceptAllCerts which allows bypassing SSL/TLS certificate validation for SMTP servers.
+  - Default value: false
+  - Warning: Enabling this option poses security risks. Only use when connecting to trusted SMTP servers with self-signed certificates.
+  - Usage: Enable only in controlled environments where certificate validation issues cannot be resolved through proper certificate installation.
🧰 Tools
🪛 Markdownlint

7-7: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


8-8: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


6-6: Expected: 2; Actual: 1
Unordered list indentation

(MD007, ul-indent)


7-7: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


8-8: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


6-6: Column: 1
Hard tabs

(MD010, no-hard-tabs)

Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs (1)

33-40: Consider additional security measures

To minimize security risks, consider these enhancements:

  1. Add runtime logging when this option is enabled
  2. Add a more visible warning mechanism (e.g., console warning) in development environments
  3. Consider adding environment-based validation to prevent usage in production

Example logging implementation:

public bool AcceptAllCerts
{
    get => _acceptAllCerts;
    set
    {
        if (value)
        {
            Logger.Warning("SSL/TLS certificate validation has been disabled. This poses significant security risks and should never be used in production.");
        }
        _acceptAllCerts = value;
    }
}
private bool _acceptAllCerts;
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (1)

Line range hint 1-272: Consider additional security measures for AcceptAllCerts feature

While the tests validate the technical functionality of AcceptAllCerts, consider implementing these additional security measures:

  1. Add runtime warnings when AcceptAllCerts is enabled
  2. Implement logging of certificate validation bypasses
  3. Consider adding a configuration validation that prevents AcceptAllCerts in production environments unless explicitly allowed
  4. Add documentation about security implications in the main README

Would you like help implementing any of these security measures?

📜 Review details

Configuration used: CodeRabbit UI
Review profile: CHILL

📥 Commits

Reviewing files that changed from the base of the PR and between 49f0b34 and 2b4fc98.

📒 Files selected for processing (4)
  • Frends.SMTP.SendEmail/CHANGELOG.md (1 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (4 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs (1 hunks)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs (3 hunks)
🚧 Files skipped from review as they are similar to previous changes (1)
  • Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/SendEmailTask.cs
🧰 Additional context used
🪛 Markdownlint
Frends.SMTP.SendEmail/CHANGELOG.md

7-7: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


8-8: Expected: 1; Actual: 4
Inconsistent indentation for list items at the same level

(MD005, list-indent)


6-6: Expected: 2; Actual: 1
Unordered list indentation

(MD007, ul-indent)


7-7: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


8-8: Expected: 2; Actual: 4
Unordered list indentation

(MD007, ul-indent)


6-6: Column: 1
Hard tabs

(MD010, no-hard-tabs)

🔇 Additional comments (4)
Frends.SMTP.SendEmail/CHANGELOG.md (1)

3-5: LGTM! Version entry follows changelog best practices

The version entry properly follows semantic versioning and clearly indicates this is a breaking change.

Frends.SMTP.SendEmail/Frends.Smtp.SendEmail/Definitions/Options.cs (1)

33-40: Implementation looks good, but warrants security attention

The implementation is well-documented with appropriate warnings and safe defaults. However, given the significant security implications, please ensure this change is:

  1. Clearly documented in release notes
  2. Highlighted in upgrade guides
  3. Communicated to users about production security risks
Frends.SMTP.SendEmail/Frends.Smtp.SendEmail.Tests/SendEmailTests.cs (2)

2-2: LGTM: Security-focused imports and safe defaults

The new imports are appropriate for SSL/TLS security handling, and the AcceptAllCerts parameter is correctly defaulted to false, following security best practices.

Also applies to: 7-10, 83-84


213-272: Comprehensive certificate validation testing, but room for improvement

The test provides good coverage of certificate validation scenarios, but could be enhanced further:

  1. Add test cases for:

    • Malformed certificates
    • Expired certificates
    • Certificate chain validation with intermediate CAs
  2. Consider adding integration tests with a self-signed certificate to validate real-world scenarios.

Please verify that these test cases adequately cover your production use cases, especially regarding self-signed certificates in your deployment environments.

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