Apple Watch Won't Launch Siri After I Upgraded iPhone

I upgraded my iPhone recently and switched carriers, but now my Apple Watch (Series 5, running WatchOS 8.5.1) no longer will connect to Siri (or Shazam) but seems to be able to communicate with iPhone. I can receive calls on the watch, I can see what music is playing on the phone, etc., I receive alerts from various apps, and texts. But if I ask Siri to do something from the Watch itself, it fails eventually.

“I’m having trouble with the connection. Please try again”

Other than nuking everything on the watch, what else should I try?

Check if Siri has been activated on the iPhone by the upgrade, if it has try to deactivate it. I might be wrong, but I belive you can’t have both activated.

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You can try flipping airplane mode on and off. But it might be easier to try restarting the watch and maybe the iPhone. Sometimes a restart fixes weird issues like this.


I’ve had Siri fail on both my Apple Watch and my Homepods with that message. Restarting seems to set everything right.

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yayyy, success!

I toggled Airport mode and pressed the side button to restart the Watch. In other words, I wasn’t scientific enough to be patient and precise and find the exact trigger which caused Siri to work again. ¯_(ツ)_/¯

I think I had tried the Airport mode trick previously though, as well as toggling Siri on/off, most likely restarting the device was the magic trick.