Why Apple Watch Update fails every time I download it?

Every time I try to download the new software update, it keeps saying, error occurred. try again. It’s happened every single time i’ve tried. Any ideas?

I don't see an option to delete the update file. Suggestions?

One additional thought:

watchOS update failed to download to the watch. The culprit was the VPN used by the iPhone. Shut off the VPN to do the watchOS update, and the update worked. Restarted VPN after watchOS update.

solved!

it keeps trying to update through the iPhone and fails, therefore:

1. Turn off your iPhone Bluetooth
2. Go to settings in your watch and under airplane mode turn off the watch bluetooth
3. turn on your iPhone hotspot
4. go to settings on your watch and under WiFi turn wifi on and connect to your iPhone hotspot
5. now go to software update and download and it works immediately

Same thing happened to me, my phone wasn’t connected to wifi at the time but when I did connect to wifi it worked.

Need more help with updating?

Try following these steps:

1. Make sure your Apple Watch is connecting to its charger correctly. 
2. Restart your Apple Watch.
3. Restart your paired iPhone.
4. Try again to update your Apple Watch.

If the update won't start:

1. Open the Apple Watch app on your iPhone.
2. Tap General > Software Update.
3. Delete the update file.
4. Try again to update your Apple Watch.

Find out what to do if you see "Cannot Install Update" when updating Apple Watch or if your Apple Watch says you need more available storage to install a watchOS update.

me too, anytime i try to download

See -> Update your Apple Watch -> Update your Apple Watch – Apple Support (UK)

• Leave your Apple Watch on its charger while it's updating. Don't restart your iPhone or Apple Watch, and don't close the Apple Watch app. When the update has completed, your Apple Watch will restart on its own.

or see:

How much free space is on your Apple Watch?

Apple Watch -> Settings -> General -> About -> Available.

It should have a few gigabytes available.

I had the same issue trying to update to OS11. It worked as soon as I connected the watch and the iPhone to the same Wi-Fi

You can manage vpn but you can not turn it off on 13 pro max

Solution works

I have tried numerous times to update watch. It has failed every time.

I told you my watch will not update.