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Still experiencing this issue on iOS 16.6. Tapping "Keep" -> "Deliver Immediately" doesn't upgrade the push permission and still stuck in delivery quietly.
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When starting the live activity you will get an error message if system fails to start the live activity. There's no way to use Xcode to preview Live Activity yet, hope Apple adds it soon.
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It's not possible with the current iOS, you will need to send a push notification to update the live activity.
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After some trial and error, it seems that the widget will auto update the date displayed but no re-layout will be done. Causing text to be truncated with ... when the display date grows longer. For example when using .relative style, display date could change from "1 sec" to "1 min 20 sec" which is much longer. If the original space doesn't fit "1 min 20 sec" then it may become "1 mi..." which looks quite bad. Quick workaround is to try allocating more space to Text element in advance.