diff --git a/spec/homesick_spec.rb b/spec/homesick_spec.rb
index 81fafb7..9e34ed3 100644
--- a/spec/homesick_spec.rb
+++ b/spec/homesick_spec.rb
@@ -169,5 +169,27 @@ describe "homesick" do
 
       some_rc_file.readlink.should == tracked_file
     end
+
+    it 'should track a file in nested folder structure' do
+      castle = given_castle('castle_repo')
+
+      some_nested_file = home.file('some/nested/file.txt')
+      homesick.track(some_nested_file.to_s, 'castle_repo')
+
+      tracked_file = castle.join('some/nested/file.txt')
+      tracked_file.should exist
+      some_nested_file.readlink.should == tracked_file
+    end
+
+    it 'should track a nested directory' do
+      castle = given_castle('castle_repo')
+
+      some_nested_dir = home.directory('some/nested/directory/')
+      homesick.track(some_nested_dir.to_s, 'castle_repo')
+
+      tracked_file = castle.join('some/nested/directory/')
+      tracked_file.should exist
+      File.realdirpath(some_nested_dir).should == File.realdirpath(tracked_file)
+    end
   end
 end