Fix for “Unable to Check for Update” when pairing an unpaired watch

I noticed many people online had this issue without many helpful solutions. I contacted Apple Support and was finally able to fix my issue, so for any people in the future that find this and need help, I hope this works for you.

The problem:

Apple Watch (in my case a Series 4) has been factory reset with all data erased (previously connected to an old phone that I don’t have anymore and I forgot the password on the watch. I had to hold down both the side button and Digital Crown until the Apple logo appeared, and then hold the side button for 30 seconds). I want to pair it to a new phone (iPhone 13 Pro, latest version). I am able to successfully connect with the phone, but I am informed I need to update the watch to go forward. However, I kept getting the popup that I am unable to do so since I am not connected to the internet.

The solution:

I needed to perform a full network settings reset. Go to Settings > General > Transfer or Reset iPhone > Reset > Reset Network Settings. This will disconnect you from all memorized WiFi networks, so you will need to reenter your password. Once your phone powers back on, go ahead and start the pairing process again.

After plenty of troubleshooting with support both over text and on the phone for over an hour, this is what finally worked. It seemed like the devices weren’t actually recognizing they were connected to the internet, even though the internet was working fine. I was finally able to move to the update screen and download watchOS 10.6.1, which is outdated but the newest available OS for the series 4. I am really hoping my experience can save the frustration of at least one other person out there. Thanks for reading!