Few more observations Seems the expired transaction receipt in question was returning a status code of 21002 when calling verifyReciept on the deprecated web API. This was causing us to flag the transaction as an error rather than accept the transaction. We've now moved over to the JWT method of verifying the receipt. As far as we can tell its not fixed the underlying issue where it's impossible to get a new subscription.

I'm having this exact same issue on testflight It used to work but recently the re-subscribe does not work.

Here's every step on how I managed to do it Prerequisites: Modern Mac (WatchOS needs a newer bluetooth module to communicate with the Mac, I used an M1 MB Air) WIFI Router Steps Plug in iPhone that has watch paired Trust the computer Add phone to Devices in Xcode Ensure WIFI for Mac, iPhone, and Watch are all joined to the same SSID and band (not a mix of 5g & 2.7ghz) Reboot watch, and unlock Unplug iPhone from computer and plug back in Accept the trust PC dialog on the watch. After 10s unplug and replug iPhone in for a second time, watch should now appear in Xcode devices. Wait for the provisioning, a yellow banner will eventually appear saying "Developer mode not enabled" On watch go to Settings -> Privacy and Security -> Developer Mode -> Enable. The watch will reboot, and then ask again to turn on Developer Mode, Accept. Then ensure the WIFI is reconnected before continuing. In Xcode Right click the watch and click reconnect. And wait for debug symbols to copy across. I had to right click and reconnect in Xcode one last time before the watch was fully provisioned.