Apple Watch stuck in update loop when pairing with iPhone

Hi everyone,

I am trying to sync my Apple Watch with my new iPhone 17 Pro Max, but I am completely stuck in an endless software update loop.

Every time I try to initiate the pairing process, the Watch app on my phone insists that the watch needs an update. However, the watch is already updated to the latest version. If I proceed with the prompt, it either hangs indefinitely or fails and asks to update all over again.

What I've already tried:

  • Force restarting both my iPhone and the Apple Watch.
  • Hard resetting the Apple Watch via the charger and Digital Crown method to start completely fresh.
  • Deleting any cached update files from the iPhone's storage settings.
  • Disabling my VPN and ensuring I am on a stable Wi-Fi connection.

Despite all this, it keeps asking for the update "a million times" and won't bypass the pairing screen. Has anyone else dealt with this specific handshake glitch on newer iOS versions, and is there a workaround to force the pairing through?

Thanks in advance!

iPhone 17 Pro Max, iOS 26

Posted on Jul 15, 2026 4:07 PM

Reply
1 reply

Jul 15, 2026 10:57 PM in response to MsPersistent

Which Apple Watch do you want to update?

Did you try to update the watch directly?

...

If your Apple Watch has watchOS 6 or later, you can install updates without your iPhone:


  1. Make sure that your watch is connected to Wi-Fi.
  2. On your watch, open the Settings app.
  3. Tap General, then tap Software Update.
  4. Tap Install if a software update is available, then follow the onscreen instructions.


...

copied from: Update your Apple Watch - Apple Support


Can you update the watch, using the old iPhone instead, and then pair it to the new iPhone 17 Pro Max?

Apple Watch stuck in update loop when pairing with iPhone

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