diff --git a/Library/Homebrew/tap.rb b/Library/Homebrew/tap.rb
index 59a4429a16..24b7a95ed9 100644
--- a/Library/Homebrew/tap.rb
+++ b/Library/Homebrew/tap.rb
@@ -299,6 +299,7 @@ class Tap
     raise TapPinStatusError.new(name, false) unless pinned?
     pinned_symlink_path.delete
     pinned_symlink_path.parent.rmdir_if_possible
+    pinned_symlink_path.parent.parent.rmdir_if_possible
     @pinned = false
   end