diff --git a/manifest.json b/manifest.json
index 8527d013..b9bb6074 100644
--- a/manifest.json
+++ b/manifest.json
@@ -1,6 +1,7 @@
 {
     "description": "RAML files listed in order corresponding RAML feature appears in RAML 1.0 spec",
     "filePaths": [
+        "tests/raml-1.0/Root/yaml-12-compliancy/invalid-old-booleans.raml",
         "tests/raml-1.0/Root/yaml-12-compliancy/valid.raml",
         "tests/raml-1.0/Root/version/invalid-version-structure.raml",
         "tests/raml-1.0/Root/version/valid.raml",
diff --git a/tests/raml-1.0/Root/yaml-12-compliancy/invalid-old-booleans.raml b/tests/raml-1.0/Root/yaml-12-compliancy/invalid-old-booleans.raml
new file mode 100644
index 00000000..2af77d97
--- /dev/null
+++ b/tests/raml-1.0/Root/yaml-12-compliancy/invalid-old-booleans.raml
@@ -0,0 +1,12 @@
+#%RAML 1.0
+
+title: Hello
+version: v1
+
+types:
+  User:
+    type: object
+    properties:
+      active:
+        type: boolean
+        enum: [y, n, yes, no]