diff --git a/lib/linguist/documentation.yml b/lib/linguist/documentation.yml
index a29a3d2f..6e06329f 100644
--- a/lib/linguist/documentation.yml
+++ b/lib/linguist/documentation.yml
@@ -10,7 +10,7 @@
 ## Documentation directories ##
 
 - ^docs?/
-- ^[Dd]ocumentation/
+- (^|/)[Dd]ocumentation/
 - (^|/)javadoc/
 - ^man/
 
diff --git a/test/test_blob.rb b/test/test_blob.rb
index ec1d6ea3..ce6cde92 100644
--- a/test/test_blob.rb
+++ b/test/test_blob.rb
@@ -449,8 +449,8 @@ class TestBlob < Minitest::Test
 
     assert_predicate fixture_blob("Documentation/foo.md"), :documentation?
     assert_predicate fixture_blob("documentation/foo.md"), :documentation?
-    refute_predicate fixture_blob("project/Documentation/foo.md"), :documentation?
-    refute_predicate fixture_blob("project/documentation/foo.md"), :documentation?
+    assert_predicate fixture_blob("project/Documentation/foo.md"), :documentation?
+    assert_predicate fixture_blob("project/documentation/foo.md"), :documentation?
 
     assert_predicate fixture_blob("javadoc/foo.html"), :documentation?
     assert_predicate fixture_blob("project/javadoc/foo.html"), :documentation?