I recently got a new phone and completely unpaired my Apple Watch, restarted it to factory settings. Now it requires an update before it will pair to my new phone, and the update never seems to finish. It has been stuck on Preparing and never updates

Hello torreyIke,

Thanks for reaching out to us in Apple Support Communities about issues updatig your Apple Watch. We're happy to help by looking into this more! 

The following support article provides some troubleshooting steps to try for this behavior: Update your Apple Watch - Apple Support

If you need help updating

Try these steps:

1. Make sure that your Apple Watch connects to its charger. 

2. 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.

3. Restart your paired iPhone.

4. Try to start the update again. 

If the update won't start, open the Watch app on your iPhone, tap General > Usage > Software Update, then delete the update file. After you delete the file, try to download and install watchOS again.

Learn what to do if you see 'Cannot Install Update' when updating Apple Watch.

Hope this helps.

Best Regards.

Hey torreyIke,

With what you've mentioned thus far, and with the steps you've already completed in mind, it might be best to Get Support directly from Apple moving forward. You can reach them with this link.

Take care.