diff --git a/errors.go b/errors.go
index 969cf3d..8c1ee6b 100644
--- a/errors.go
+++ b/errors.go
@@ -13,6 +13,15 @@ import (
 )
 
 var (
+	// ErrExpectedMapOrYAMLString is returned when a field that can contain a
+	// map[string]interface{} or an embedded YAML string did not contain either
+	// of those things.
+	// TODO(jaypipes): Move to gdt core?
+	ErrExpectedMapOrYAMLString = fmt.Errorf(
+		"%w: expected either map[string]interface{} "+
+			"or a string with embedded YAML",
+		gdterrors.ErrParse,
+	)
 	// ErrMoreThanOneShortcut is returned when the test author included
 	// more than one shortcut (e.g. `kube.create` or `kube.apply`) in the same
 	// test spec.
@@ -119,6 +128,15 @@ var (
 	)
 )
 
+// ExpectedMapOrYAMLStringAt returns ErrExpectedMapOrYAMLString for a given
+// YAML node
+func ExpectedMapOrYAMLStringAt(node *yaml.Node) error {
+	return fmt.Errorf(
+		"%w at line %d, column %d",
+		ErrExpectedMapOrYAMLString, node.Line, node.Column,
+	)
+}
+
 // KubeConfigNotFound returns ErrKubeConfigNotFound for a given filepath
 func KubeConfigNotFound(path string) error {
 	return fmt.Errorf("%w: %s", ErrKubeConfigNotFound, path)
diff --git a/eval.go b/eval.go
index 48f58d7..7104bf2 100644
--- a/eval.go
+++ b/eval.go
@@ -16,6 +16,7 @@ import (
 	"time"
 
 	backoff "github.com/cenkalti/backoff/v4"
+	gdtcontext "github.com/gdt-dev/gdt/context"
 	"github.com/gdt-dev/gdt/debug"
 	gdterrors "github.com/gdt-dev/gdt/errors"
 	"github.com/gdt-dev/gdt/parse"
@@ -60,6 +61,16 @@ func (s *Spec) Eval(ctx context.Context, t *testing.T) *result.Result {
 		if s.Kube.Apply != "" {
 			res = s.apply(ctx, t, c)
 		}
+		for _, failure := range res.Failures() {
+			if gdtcontext.TimedOut(ctx, failure) {
+				to := s.Timeout
+				if to != nil && !to.Expected {
+					t.Error(gdterrors.TimeoutExceeded(to.After, failure))
+				}
+			} else {
+				t.Error(failure)
+			}
+		}
 	})
 	return res
 }
diff --git a/eval_test.go b/eval_test.go
index aedb3f5..58f6484 100644
--- a/eval_test.go
+++ b/eval_test.go
@@ -5,7 +5,6 @@
 package kube_test
 
 import (
-	"context"
 	"os"
 	"path/filepath"
 	"testing"
@@ -13,40 +12,9 @@ import (
 	"github.com/gdt-dev/gdt"
 	gdtcontext "github.com/gdt-dev/gdt/context"
 	kindfix "github.com/gdt-dev/kube/fixtures/kind"
-	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 )
 
-func TestUnknownKubeContextInSpec(t *testing.T) {
-	require := require.New(t)
-	assert := assert.New(t)
-
-	fp := filepath.Join("testdata", "parse", "fail", "unknown-context.yaml")
-
-	s, err := gdt.From(fp)
-	require.Nil(err)
-	require.NotNil(s)
-
-	err = s.Run(context.TODO(), t)
-	assert.NotNil(err)
-	assert.ErrorContains(err, "context \"unknownctx\" does not exist")
-}
-
-func TestUnknownKubeContextInDefaults(t *testing.T) {
-	require := require.New(t)
-	assert := assert.New(t)
-
-	fp := filepath.Join("testdata", "parse", "fail", "unknown-context-in-defaults.yaml")
-
-	s, err := gdt.From(fp)
-	require.Nil(err)
-	require.NotNil(s)
-
-	err = s.Run(context.TODO(), t)
-	require.NotNil(err)
-	assert.ErrorContains(err, "context \"unknownctx\" does not exist")
-}
-
 func TestListPodsEmpty(t *testing.T) {
 	skipIfKind(t)
 	require := require.New(t)
diff --git a/go.mod b/go.mod
index ac43620..bc1fbe9 100644
--- a/go.mod
+++ b/go.mod
@@ -4,7 +4,7 @@ go 1.19
 
 require (
 	github.com/cenkalti/backoff/v4 v4.2.1
-	github.com/gdt-dev/gdt v1.1.0
+	github.com/gdt-dev/gdt v1.1.1
 	github.com/samber/lo v1.38.1
 	github.com/stretchr/testify v1.8.4
 	gopkg.in/yaml.v3 v3.0.1
diff --git a/go.sum b/go.sum
index 7d72a9f..224bdcc 100644
--- a/go.sum
+++ b/go.sum
@@ -65,8 +65,8 @@ github.com/envoyproxy/protoc-gen-validate v0.1.0/go.mod h1:iSmxcyjqTsJpI2R4NaDN7
 github.com/evanphx/json-patch v4.12.0+incompatible h1:4onqiflcdA9EOZ4RxV643DvftH5pOlLGNtQ5lPWQu84=
 github.com/evanphx/json-patch/v5 v5.6.0 h1:b91NhWfaz02IuVxO9faSllyAtNXHMPkC5J8sJCLunww=
 github.com/evanphx/json-patch/v5 v5.6.0/go.mod h1:G79N1coSVB93tBe7j6PhzjmR3/2VvlbKOFpnXhI9Bw4=
-github.com/gdt-dev/gdt v1.1.0 h1:+eFYFSibOYCTFKqoACx2CefAbErmBmFWXG7kDioR5do=
-github.com/gdt-dev/gdt v1.1.0/go.mod h1:StnyGjC/67u59La2u6fh3HwW9MmodVhKdXcLlkgvNSY=
+github.com/gdt-dev/gdt v1.1.1 h1:863WjQr2Oa+1eVKJspw1SRqW72S0Y3UydN0j8WwPYJU=
+github.com/gdt-dev/gdt v1.1.1/go.mod h1:StnyGjC/67u59La2u6fh3HwW9MmodVhKdXcLlkgvNSY=
 github.com/go-gl/glfw v0.0.0-20190409004039-e6da0acd62b1/go.mod h1:vR7hzQXu2zJy9AVAgeJqvqgH9Q5CA+iKCZ2gyEVpxRU=
 github.com/go-gl/glfw/v3.3/glfw v0.0.0-20191125211704-12ad95a8df72/go.mod h1:tQ2UAYgL5IevRw8kRxooKSPJfGvJ9fJQFa0TUsXzTg8=
 github.com/go-gl/glfw/v3.3/glfw v0.0.0-20200222043503-6f7a984d4dc4/go.mod h1:tQ2UAYgL5IevRw8kRxooKSPJfGvJ9fJQFa0TUsXzTg8=
diff --git a/parse.go b/parse.go
index 6bf8cce..eee74a6 100644
--- a/parse.go
+++ b/parse.go
@@ -8,6 +8,7 @@ import (
 	"os"
 	"strings"
 
+	gdtjson "github.com/gdt-dev/gdt/assertion/json"
 	"github.com/gdt-dev/gdt/errors"
 	gdttypes "github.com/gdt-dev/gdt/types"
 	"github.com/samber/lo"
@@ -84,6 +85,109 @@ func (s *Spec) UnmarshalYAML(node *yaml.Node) error {
 	return nil
 }
 
+func (e *Expect) UnmarshalYAML(node *yaml.Node) error {
+	if node.Kind != yaml.MappingNode {
+		return errors.ExpectedMapAt(node)
+	}
+	// maps/structs are stored in a top-level Node.Content field which is a
+	// concatenated slice of Node pointers in pairs of key/values.
+	for i := 0; i < len(node.Content); i += 2 {
+		keyNode := node.Content[i]
+		if keyNode.Kind != yaml.ScalarNode {
+			return errors.ExpectedScalarAt(keyNode)
+		}
+		key := keyNode.Value
+		valNode := node.Content[i+1]
+		switch key {
+		case "error":
+			if valNode.Kind != yaml.ScalarNode {
+				return errors.ExpectedScalarAt(valNode)
+			}
+			var v string
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.Error = v
+		case "len":
+			if valNode.Kind != yaml.ScalarNode {
+				return errors.ExpectedScalarAt(valNode)
+			}
+			var v *int
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.Len = v
+		case "unknown":
+			if valNode.Kind != yaml.ScalarNode {
+				return errors.ExpectedScalarAt(valNode)
+			}
+			var v bool
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.Unknown = v
+		case "notfound":
+			if valNode.Kind != yaml.ScalarNode {
+				return errors.ExpectedScalarAt(valNode)
+			}
+			var v bool
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.NotFound = v
+		case "json":
+			if valNode.Kind != yaml.MappingNode {
+				return errors.ExpectedMapAt(valNode)
+			}
+			var v *gdtjson.Expect
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.JSON = v
+		case "conditions":
+			if valNode.Kind != yaml.MappingNode {
+				return errors.ExpectedMapAt(valNode)
+			}
+			var v map[string]*ConditionMatch
+			if err := valNode.Decode(&v); err != nil {
+				return err
+			}
+			e.Conditions = v
+		case "matches":
+			if valNode.Kind == yaml.MappingNode {
+				var v map[string]interface{}
+				if err := valNode.Decode(&v); err != nil {
+					return err
+				}
+				e.Matches = v
+			} else if valNode.Kind == yaml.ScalarNode {
+				if valNode.Tag == "!!null" {
+					return ExpectedMapOrYAMLStringAt(valNode)
+				}
+				var v string
+				if err := valNode.Decode(&v); err != nil {
+					return err
+				}
+				if err := validateFileExists(v); err != nil {
+					return err
+				}
+				// inline YAML. check it can be unmarshaled into a
+				// map[string]interface{}
+				var m map[string]interface{}
+				if err := yaml.Unmarshal([]byte(v), &m); err != nil {
+					return MatchesInvalidUnmarshalError(err)
+				}
+				e.Matches = m
+			} else {
+				return ExpectedMapOrYAMLStringAt(valNode)
+			}
+		default:
+			return errors.UnknownFieldAt(key, keyNode)
+		}
+	}
+	return nil
+}
+
 // validateShortcuts ensures that the test author has specified only a single
 // shortcut (e.g. `kube.create`) and that if a shortcut is specified, any
 // long-form KubeSpec is not present.
@@ -198,14 +302,6 @@ func validateKubeSpec(s *Spec) error {
 			}
 		}
 	}
-	if s.Assert != nil {
-		exp := s.Assert
-		if exp.Matches != nil {
-			if err := validateMatches(exp.Matches); err != nil {
-				return err
-			}
-		}
-	}
 	return nil
 }
 
@@ -254,29 +350,3 @@ func validateResourceIdentifier(subject string) error {
 	}
 	return nil
 }
-
-// validateMatches checks what the test author placed in the `Kube.Matches`
-// field to see if it contains one of:
-// * file path (and checks existence of this file)
-// * inline YAML (and checks that can be unmarshaled)
-// * map[string]interface{}
-func validateMatches(matches interface{}) error {
-	switch matches.(type) {
-	case string:
-		v := matches.(string)
-		if probablyFilePath(v) {
-			return validateFileExists(v)
-		}
-		// inline YAML. Let's quickly check it can be unmarshaled into a
-		// map[string]interface{}
-		var m map[string]interface{}
-		if err := yaml.Unmarshal([]byte(v), &m); err != nil {
-			return MatchesInvalidUnmarshalError(err)
-		}
-	case map[string]interface{}:
-		return nil
-	default:
-		return MatchesInvalid(matches)
-	}
-	return nil
-}
diff --git a/parse_test.go b/parse_test.go
index b47b53e..284e962 100644
--- a/parse_test.go
+++ b/parse_test.go
@@ -22,7 +22,7 @@ func currentDir() string {
 	return filepath.Dir(filename)
 }
 
-func TestBadDefaults(t *testing.T) {
+func TestFailureBadDefaults(t *testing.T) {
 	assert := assert.New(t)
 	require := require.New(t)
 
@@ -138,7 +138,7 @@ func TestFailureCreateFileNotFound(t *testing.T) {
 	require.Nil(s)
 }
 
-func TestDeleteFileNotFound(t *testing.T) {
+func TestFailureDeleteFileNotFound(t *testing.T) {
 	require := require.New(t)
 	assert := assert.New(t)
 
@@ -177,6 +177,19 @@ func TestFailureBadMatchesInvalidYAML(t *testing.T) {
 	require.Nil(s)
 }
 
+func TestFailureBadMatchesEmpty(t *testing.T) {
+	assert := assert.New(t)
+	require := require.New(t)
+
+	fp := filepath.Join("testdata", "parse", "fail", "bad-matches-empty.yaml")
+
+	s, err := gdt.From(fp)
+	require.NotNil(err)
+	assert.ErrorIs(err, gdtkube.ErrExpectedMapOrYAMLString)
+	assert.ErrorIs(err, errors.ErrParse)
+	require.Nil(s)
+}
+
 func TestFailureBadMatchesNotMapAny(t *testing.T) {
 	assert := assert.New(t)
 	require := require.New(t)
diff --git a/testdata/parse/fail/bad-matches-empty.yaml b/testdata/parse/fail/bad-matches-empty.yaml
new file mode 100644
index 0000000..cfa1a26
--- /dev/null
+++ b/testdata/parse/fail/bad-matches-empty.yaml
@@ -0,0 +1,7 @@
+name: bad-matches-empty
+description: "matches is not a string or map[string]interface{}"
+tests:
+ - kube:
+     get: pods/mypod
+   assert:
+     matches:
diff --git a/testdata/parse/fail/unknown-context-in-defaults.yaml b/testdata/parse/fail/unknown-context-in-defaults.yaml
deleted file mode 100644
index efb9866..0000000
--- a/testdata/parse/fail/unknown-context-in-defaults.yaml
+++ /dev/null
@@ -1,9 +0,0 @@
-name: unknown-context-in-defaults
-description: unknown kubecontext specified in defaults
-defaults:
-  kube:
-     context: unknownctx
-tests:
- - kube:
-     create: testdata/manifests/nginx-pod.yaml
-
diff --git a/testdata/parse/fail/unknown-context.yaml b/testdata/parse/fail/unknown-context.yaml
deleted file mode 100644
index 70a474f..0000000
--- a/testdata/parse/fail/unknown-context.yaml
+++ /dev/null
@@ -1,6 +0,0 @@
-name: unknown-context
-description: unknown kubecontext specified in spec
-tests:
- - kube:
-     create: testdata/manifests/nginx-pod.yaml
-     context: unknownctx