diff --git a/Sources/OpenAPIKit/Validator/Validator.swift b/Sources/OpenAPIKit/Validator/Validator.swift
index 07f153a238..4b8c5fadea 100644
--- a/Sources/OpenAPIKit/Validator/Validator.swift
+++ b/Sources/OpenAPIKit/Validator/Validator.swift
@@ -424,6 +424,10 @@ class _ReferencingValidator: _Validator {
             userInfo: encoder.userInfo,
             codingPath: encoder.codingPath + [key]
         )
+        if let typedKey = key as? AnyCodingKey,
+            let validatableKey = typedKey.originalValue as? Validatable {
+              applyValidations(to: validatableKey)
+        }
     }
 
     init(referencing encoder: _Validator, at index: Int) {
@@ -573,7 +577,7 @@ extension _Validator: SingleValueEncodingContainer {
         )
     }
 
-    fileprivate func applyValidations(to value: Encodable, atKey key: CodingKey? = nil) {
+    fileprivate func applyValidations(to value: Any, atKey key: CodingKey? = nil) {
         let pathTail = key.map { [$0] } ?? []
         for idx in validations.indices {
             errors += validations[idx].apply(to: value, at: codingPath + pathTail, in: document)
diff --git a/Sources/OpenAPIKitCore/OrderedDictionary/OrderedDictionary.swift b/Sources/OpenAPIKitCore/OrderedDictionary/OrderedDictionary.swift
index ffadaf3932..1b9eedf8bb 100644
--- a/Sources/OpenAPIKitCore/OrderedDictionary/OrderedDictionary.swift
+++ b/Sources/OpenAPIKitCore/OrderedDictionary/OrderedDictionary.swift
@@ -282,9 +282,16 @@ extension OrderedDictionary: Sendable where Key: Sendable, Value: Sendable {}
 public struct AnyCodingKey: CodingKey {
 
     public let stringValue: String
+    public let originalValue: Any
 
     public init(stringValue: String) {
         self.stringValue = stringValue
+        self.originalValue = stringValue
+    }
+
+    public init(stringValue: String, originalValue: Any) {
+        self.stringValue = stringValue
+        self.originalValue = originalValue
     }
 
     public let intValue: Int? = nil
@@ -327,7 +334,8 @@ extension OrderedDictionary: Encodable where Key: Encodable, Value: Encodable {
 
         // try for RawRepresentable with String RawValues
         if let encodableDictionary = self as? StringRawKeyEncodable {
-            let kvPairs = zip(encodableDictionary.orderedStringKeys, self.values)
+            let keyPairs = zip(self.orderedKeys, encodableDictionary.orderedStringKeys)
+            let kvPairs = zip(keyPairs, self.values)
             try encodeKeyValuePairs(kvPairs, to: encoder)
             return
         }
@@ -365,15 +373,16 @@ internal func encodeKeyValuePairs<Value: Encodable>(
     }
 }
 
-/// Encode a sequence of `String`/`Value` pairs as a hash.
-internal func encodeKeyValuePairs<Value: Encodable>(
-    _ keyValuePairs: Zip2Sequence<[String], [Value]>,
+/// Encode a sequence of `String`/`Value` pairs as a hash keeping track of the
+/// original RawRepresentable values.
+internal func encodeKeyValuePairs<Value: Encodable, T>(
+    _ keyValuePairs: Zip2Sequence<Zip2Sequence<[T], [String]>, [Value]>,
     to encoder: Encoder
 ) throws {
     var container = encoder.container(keyedBy: AnyCodingKey.self)
 
     for (key, value) in keyValuePairs {
-        try container.encode(value, forKey: .init(stringValue: key))
+        try container.encode(value, forKey: .init(stringValue: key.1, originalValue: key.0))
     }
 }
 
diff --git a/Tests/OpenAPIKitTests/Validator/ValidatorTests.swift b/Tests/OpenAPIKitTests/Validator/ValidatorTests.swift
index 5a8bfc0163..ca0ca3c227 100644
--- a/Tests/OpenAPIKitTests/Validator/ValidatorTests.swift
+++ b/Tests/OpenAPIKitTests/Validator/ValidatorTests.swift
@@ -1086,6 +1086,32 @@ final class ValidatorTests: XCTestCase {
         try document.validate(using: validator)
     }
 
+    func test_keyedContainerKeysAreValidated() {
+        let contentMap : OpenAPI.Content.Map = [
+            .json: .a(.component(named: "jsonContent"))
+        ]
+        let doc = OpenAPI.Document(
+            info: .init(title: "doc", version: "1.0"),
+            servers: [],
+            paths: [
+                "/hello": .init(
+                    summary: "test",
+                    get: .init(responses: [
+                        200: .response(content: contentMap)
+                    ])
+                )
+            ],
+            components: .noComponents
+        )
+        let notJson = Validation<OpenAPI.ContentType>.init(description: "JSON content not allowed", check: \.rawValue != "application/json")
+
+        XCTAssertThrowsError(try doc.validate(using: Validator.blank.validating(notJson), strict: false)) { error in
+            let error = error as? ValidationErrorCollection
+
+            XCTAssertEqual(error.map(OpenAPI.Error.init(from:))?.localizedDescription, "Failed to satisfy: JSON content not allowed at path: .paths[\'/hello\'].get.responses.200.content[\'application/json\']")
+        }
+    }
+
     /// This test confirms the last example in the validation documentation file (documentation/validation.md)
     /// functions as-written.
     func test_requestBodySchemaValidationFails() {