This problem keeps happening to me using ArcGIS Pro SDK. I read that it may be a issue with the SDK Pro v.2.8. After I created a dockpane application, it will work in Pro, but after making some edits to the dockpaneViewModel and dockpane. xaml, I tried to test the tool again, and the dockpane button no longer works. After making the edits, I don't have any problem rebuilding the tool. I am wondering if anyone else have this issue as well?