I used to be able to do this, and I'm not sure if it was the recent Windows update that broke it or if it happened before that. But I just noticed that I can no longer right-click an icon (for example, to choose "Pin to Taskbar") when the taskbar is placed at the top of the Monitor. If I move the position to the bottom then right-clicking works as expected.
I just upgraded to Start11 v2 (from v1.5) and it did not fix the issue 
Is there anything that can be done about this?