Hi ras12o,
I understand that you are trying to update your Apple Watch, but your iPhone is showing increasingly longer estimatedtimesto complete this process. I'm happy to provide some help for this issue.
You've done well to restart your iPhone already to troubleshoot this issue. I recommend following all of the steps outlined in the following article for this issue:
Update your Apple Watch - Apple Support
Try these steps:
- Make sure that your Apple Watch connects to its charger.
- Restart your Apple Watch. Press and hold the side button until you see Power Off, then drag the slider. To turn your watch on again, press and hold the side button.
- Restart your paired iPhone. Press and hold the Sleep/Wake button until the red slider appears, then drag the slider. To turn your iPhone on again, press and hold the Sleep/Wake button.
- Try to start the update again.
If the update won't start, open the Apple Watch app on your iPhone, tap General > Usage > Software Update, then delete the update file. After you delete the file, try to download and installwatchOSagain.
Thanks for using the Apple Support Communities. Cheers!