Just to clarify: I'm not using receipt validation. Just submitting an SKPayment with my product, which keeps on failing.
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It turns out I was calling things in the wrong order, you need to follow https://developer.apple.com/documentation/storekit/in-app_purchase/setting_up_the_transaction_observer_for_the_payment_queue *exactly*
I've noticed this too! https://developer.apple.com/forums/thread/652946
Right now I'm foregrounding the app every time I need to update the widget, which is not very nice of course.