diff --git a/lib/linguist/documentation.yml b/lib/linguist/documentation.yml
index 04649b5b..230cd423 100644
--- a/lib/linguist/documentation.yml
+++ b/lib/linguist/documentation.yml
@@ -22,7 +22,9 @@
 - (^|/)COPYING(\.|$)
 - (^|/)INSTALL(\.|$)
 - (^|/)LICEN[CS]E(\.|$)
+- (^|/)[Ll]icen[cs]e(\.|$)
 - (^|/)README(\.|$)
+- (^|/)[Rr]eadme(\.|$)
 
 # Samples folders
 - ^[Ss]amples/
diff --git a/test/test_blob.rb b/test/test_blob.rb
index 6c705379..0a1cefe9 100644
--- a/test/test_blob.rb
+++ b/test/test_blob.rb
@@ -514,6 +514,8 @@ class TestBlob < Minitest::Test
     assert_predicate fixture_blob("README"), :documentation?
     assert_predicate fixture_blob("README.md"), :documentation?
     assert_predicate fixture_blob("README.txt"), :documentation?
+    assert_predicate fixture_blob("Readme"), :documentation?
+    assert_predicate fixture_blob("readme"), :documentation?
     assert_predicate fixture_blob("foo/README"), :documentation?
 
     assert_predicate fixture_blob("CHANGE"), :documentation?
@@ -541,6 +543,7 @@ class TestBlob < Minitest::Test
 
     assert_predicate fixture_blob("LICENSE"), :documentation?
     assert_predicate fixture_blob("LICENCE.md"), :documentation?
+    assert_predicate fixture_blob("License.txt"), :documentation?
     assert_predicate fixture_blob("LICENSE.txt"), :documentation?
     assert_predicate fixture_blob("foo/LICENSE"), :documentation?