What to do if updating an Apple Watch with watchOS 6 fails

There is a known incompatibility between the current iOS 14 version and older back level versions of watchOS 6. Trying to update an Apple Watch with that watchOS version may fail at critical step right after unpairing. Typically there is a message of not being connected to Internet even when that is not the case.

In that situation it is best to contact Apple Support or visit an Apple store and ask if they can complete that update for you.

Alternatively, if you happen to have an old iPhone with iOS 12 still around, you could try pairing with that first. After the update to the current watchOS 7.5 is complete, you can pair again with your iPhone, restoring your backup that was taken during the original unpairing.