There is a bug since watchOS 8 where it prompts you to give access to the shortcut on every run.
The message may appear like:
- Allow ”<shortcut name>” to access “Due”?
- Allow ”<shortcut name>” to access (null)?
Even after choosing ‘Allow’, watchOS fails to remember your choice and continues to prompt you for access each time you attempt to use the shortcut.
This is a bug introduced in watchOS 8 / iOS 15. We've filed a report with Apple (FB9894986 - Shortcut prompts for access on every execution if companion Watch app is installed). The bug persists in watchOS 9 and iOS 16.
Workaround
The only workaround for this issue is to uninstall the Due Watch companion app. This causes watchOS to remember your choice and to not prompt you on every run. Obviously this is not ideal if you rely on complications or the Due companion watch app.
2024 Update (iOS 17 and watchOS 10)
A user reported that the problem has been resolved in watchOS 10 and iOS 17 after manually re-creating the shortcut. (thanks John L.)