Apple Watch Series 10: watchOS 26.5 update stuck, won't pair

Hi everyone,

I’m having a frustrating issue with my Apple Watch Series 10 while trying to update to watchOS 26.5. I’m currently stuck in a loop and haven't been able to use my watch for hours.

The Problem:

During the update process, the Watch app on my iPhone stays stuck on "Checking for Updates" for an indefinite amount of time. Occasionally, it manages to show a download bar, but then gives an estimated time of "5 hours remaining" (or more) and eventually fails or just hangs there.

Because I tried to unpair and re-pair the watch to fix this, I am now stuck on the "Update Required" screen during the initial setup. I cannot complete the pairing process because the update won't download, effectively leaving my watch "bricked" and unusable.

What I’ve already tried (none worked):

• Hard Reset: Restarted both iPhone and Watch (Digital Crown + Side button).
• Unpairing/Re-pairing: Currently stuck in the middle of this.
• Bluetooth Toggling: Tried turning Bluetooth off/on in iOS Settings.
• Network: Switched between different Wi-Fi networks (2.4GHz and 5GHz).
• iPhone Update: My iPhone is already running the latest iOS version.
• Charging: The watch is on the charger and at 100% battery.

Has anyone else encountered this with watchOS 26.5 on the Series 10? Is this a known server-side issue with Apple, or is there a workaround to skip the update during setup?

Any help would be greatly appreciated!