diff --git a/Taskfile.yml b/Taskfile.yml
index d22a197..ed85e48 100644
--- a/Taskfile.yml
+++ b/Taskfile.yml
@@ -328,6 +328,9 @@ tasks:
             # We need to replace localhost with the registry container name as it is how
             # the registry is reachable from within the Docker network.
             sh: sed -E 's/^localhost/{{ .REGISTRY_NAME }}/;t' <<< "{{ .EXTENSION_IMAGE }}"
+    requires:
+      vars:
+        - name: TARGET
 
   e2e:test:
     desc: Test target extension using Chainsaw
diff --git a/dagger/maintenance/main.go b/dagger/maintenance/main.go
index 508c722..618c407 100644
--- a/dagger/maintenance/main.go
+++ b/dagger/maintenance/main.go
@@ -136,6 +136,10 @@ func (m *Maintenance) GetTargets(
 // Generates Chainsaw's testing external values in YAML format
 func (m *Maintenance) GenerateTestingValues(
 	ctx context.Context,
+	// The source directory containing the extension folders. Defaults to the current directory
+	// +ignore=["dagger", ".github"]
+	// +defaultPath="/"
+	source *dagger.Directory,
 	// Path to the target extension directory
 	target *dagger.Directory,
 	// URL reference to the extension image to test [REPOSITORY[:TAG]]
@@ -174,18 +178,19 @@ func (m *Maintenance) GenerateTestingValues(
 			targetExtensionImage)
 	}
 
+	extensions, err := generateTestingValuesExtensions(ctx, source, metadata, targetExtensionImage)
+	if err != nil {
+		return nil, err
+	}
+
 	// Build values.yaml content
 	values := map[string]any{
 		"name":                     metadata.Name,
 		"sql_name":                 metadata.SQLName,
-		"image_name":               metadata.ImageName,
 		"shared_preload_libraries": metadata.SharedPreloadLibraries,
-		"extension_control_path":   metadata.ExtensionControlPath,
-		"dynamic_library_path":     metadata.DynamicLibraryPath,
-		"ld_library_path":          metadata.LdLibraryPath,
-		"extension_image":          targetExtensionImage,
 		"pg_image":                 pgImage,
 		"version":                  version,
+		"extensions":               extensions,
 	}
 	valuesYaml, err := yaml.Marshal(values)
 	if err != nil {
diff --git a/dagger/maintenance/parse.go b/dagger/maintenance/parse.go
index d82dd81..82611b9 100644
--- a/dagger/maintenance/parse.go
+++ b/dagger/maintenance/parse.go
@@ -3,6 +3,7 @@ package main
 import (
 	"context"
 	"encoding/json"
+	"fmt"
 	"path"
 
 	"github.com/docker/buildx/bake"
@@ -28,6 +29,7 @@ type extensionMetadata struct {
 	DynamicLibraryPath     []string   `hcl:"dynamic_library_path" cty:"dynamic_library_path"`
 	LdLibraryPath          []string   `hcl:"ld_library_path" cty:"ld_library_path"`
 	AutoUpdateOsLibs       bool       `hcl:"auto_update_os_libs" cty:"auto_update_os_libs"`
+	RequiredExtensions     []string   `hcl:"required_extensions" cty:"required_extensions"`
 	Versions               versionMap `hcl:"versions" cty:"versions"`
 	Remain                 hcl.Body   `hcl:",remain"`
 }
@@ -91,6 +93,14 @@ func parseExtensionMetadata(ctx context.Context, extensionDirectory *dagger.Dire
 		Remain   hcl.Body          `hcl:",remain"`
 	}
 
+	hasMetadataFile, err := extensionDirectory.Exists(ctx, metadataFile)
+	if err != nil {
+		return nil, err
+	}
+	if !hasMetadataFile {
+		return nil, fmt.Errorf("metadata.hcl file is missing")
+	}
+
 	data, err := extensionDirectory.File(metadataFile).Contents(ctx)
 	if err != nil {
 		return nil, err
diff --git a/dagger/maintenance/testingvalues.go b/dagger/maintenance/testingvalues.go
new file mode 100644
index 0000000..33ec68c
--- /dev/null
+++ b/dagger/maintenance/testingvalues.go
@@ -0,0 +1,60 @@
+package main
+
+import (
+	"context"
+	"fmt"
+
+	"dagger/maintenance/internal/dagger"
+)
+
+func generateTestingValuesExtensions(ctx context.Context, source *dagger.Directory, metadata *extensionMetadata, extensionImage string) ([]map[string]any, error) {
+	var out []map[string]any
+	configuration, err := generateExtensionConfiguration(metadata, extensionImage)
+	if err != nil {
+		return nil, err
+	}
+	out = append(out, configuration)
+
+	for _, dep := range metadata.RequiredExtensions {
+		depExists, err := source.Exists(ctx, dep)
+		if err != nil {
+			return nil, err
+		}
+		if !depExists {
+			return nil, fmt.Errorf("required dependency %q not found", dep)
+		}
+
+		depMetadata, parseErr := parseExtensionMetadata(ctx, source.Directory(dep))
+		if parseErr != nil {
+			return nil, fmt.Errorf("failed to parse dependency metadata %q: %w", dep, parseErr)
+		}
+		depsConfiguration, extErr := generateExtensionConfiguration(depMetadata, "")
+		if extErr != nil {
+			return nil, extErr
+		}
+		out = append(out, depsConfiguration)
+	}
+
+	return out, nil
+}
+
+func generateExtensionConfiguration(metadata *extensionMetadata, extensionImage string) (map[string]any, error) {
+	targetExtensionImage := extensionImage
+	if targetExtensionImage == "" {
+		var err error
+		targetExtensionImage, err = getDefaultExtensionImage(metadata)
+		if err != nil {
+			return nil, err
+		}
+	}
+
+	return map[string]any{
+		"name": metadata.Name,
+		"image": map[string]string{
+			"reference": targetExtensionImage,
+		},
+		"extension_control_path": metadata.ExtensionControlPath,
+		"dynamic_library_path":   metadata.DynamicLibraryPath,
+		"ld_library_path":        metadata.LdLibraryPath,
+	}, nil
+}
diff --git a/pgaudit/metadata.hcl b/pgaudit/metadata.hcl
index 7cdf53a..ba2a970 100644
--- a/pgaudit/metadata.hcl
+++ b/pgaudit/metadata.hcl
@@ -7,6 +7,7 @@ metadata = {
   dynamic_library_path     = []
   ld_library_path          = []
   auto_update_os_libs      = false
+  required_extensions      = []
 
   versions = {
     bookworm = {
diff --git a/pgvector/metadata.hcl b/pgvector/metadata.hcl
index c8ca281..965b403 100644
--- a/pgvector/metadata.hcl
+++ b/pgvector/metadata.hcl
@@ -7,6 +7,7 @@ metadata = {
   dynamic_library_path     = []
   ld_library_path          = []
   auto_update_os_libs      = false
+  required_extensions      = []
 
   versions = {
     bookworm = {
diff --git a/postgis/metadata.hcl b/postgis/metadata.hcl
index be8de2c..9f2156c 100644
--- a/postgis/metadata.hcl
+++ b/postgis/metadata.hcl
@@ -7,6 +7,7 @@ metadata = {
   dynamic_library_path     = []
   ld_library_path          = ["/system"]
   auto_update_os_libs      = true
+  required_extensions      = []
 
   versions = {
     bookworm = {
diff --git a/postgis/test/cluster.yaml b/postgis/test/cluster.yaml
index 779b4a1..1a06cd3 100644
--- a/postgis/test/cluster.yaml
+++ b/postgis/test/cluster.yaml
@@ -11,10 +11,4 @@ spec:
 
   postgresql:
     shared_preload_libraries: ($values.shared_preload_libraries)
-    extensions:
-      - name: ($values.name)
-        image:
-          reference: ($values.extension_image)
-        extension_control_path: ($values.extension_control_path)
-        dynamic_library_path: ($values.dynamic_library_path)
-        ld_library_path: ($values.ld_library_path)
+    extensions: ($values.extensions)
diff --git a/templates/metadata.hcl.tmpl b/templates/metadata.hcl.tmpl
index d6f800f..cffc0ea 100644
--- a/templates/metadata.hcl.tmpl
+++ b/templates/metadata.hcl.tmpl
@@ -9,6 +9,7 @@ metadata = {
   dynamic_library_path     = []
   ld_library_path          = []
   auto_update_os_libs      = false
+  required_extensions      = []
 
   versions = {
     {{- range $distro := .Distros}}
diff --git a/test/cluster.yaml b/test/cluster.yaml
index 779b4a1..1a06cd3 100644
--- a/test/cluster.yaml
+++ b/test/cluster.yaml
@@ -11,10 +11,4 @@ spec:
 
   postgresql:
     shared_preload_libraries: ($values.shared_preload_libraries)
-    extensions:
-      - name: ($values.name)
-        image:
-          reference: ($values.extension_image)
-        extension_control_path: ($values.extension_control_path)
-        dynamic_library_path: ($values.dynamic_library_path)
-        ld_library_path: ($values.ld_library_path)
+    extensions: ($values.extensions)