Thanks for the information. We also use a lot of context menus in our software. My current workaround is to use the X,Y coordinates within the context menu. Not ideal but it will work for the time being.
I reached out to support to see if there is something I am missing and/or not understanding. It could be an issue with TestComplete dealing with complex context menus. I ran their notepad example https://support.smartbear.com/testcomplete/docs/app-objects/specific-tasks/standard/menu/displaying-... and that seemed to work just fine. I tried replicating what they did within our software but I had no luck. Even had one of the developers take a look and they were stumped and just suggested I use the X,Y coordinates.