If I'm reading this correctly you're passing in Date() for all of your entries. My understanding of the API is that you need to project into the future what the values will be by incrementing your Date() for each of the next 14 minutes. I get that you're setting nextUpdateDate, but again I understood this to be that it's reading your date on the .end of the individual entries as the date it needs to refresh.
rodericthumbworks
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It sounds like your normal process is to build and run the App scheme, then once the app is on the simulator, you're enabling the app jiggling, then tapping the + button. The response to your question was, don't build the app scheme, build the widget kit extensions scheme. You can change your scheme by tapping the pulldown in Xcode that is next to the large play button and square stop button on the top left of your Xcode window. In the emoji ranger app it shows either the icon for the app which is like a panda on an orange background or you can select the 2 widget options which don't have an app icon. If you see the panda on your Xcode window you're building the app scheme, not the extension scheme.