I found this out eventually by looking at the IceCubes open source app on Github. The initial look at the share extension documentation was not super clear it was for inbound share. I had tried to use the older accepted documents types from the objective-C days and it is superseded by new share extension plist. Now I am off to figure out the reception part of finding out how to capture the share. Picking apart NSExtensionItem

I ran Into these. deleted the simulator default.store files deleted the derived data for the app deleted all the cached simulators stuff in derived data. quit and restart Xcode launch app on the simulator and recreated the store. All gone for now.Obviously I used a big hammer but it worked.