[Apple Watch] Unable to Check for Update - Not connected to the internet error

I did try resetting phone and erasing all content on apple watch - did not work.
I also tried signing out of iCloud and signing back in - did not work.
I tried forgetting internet, reset router - did not work.
I went into settings and changed my region from United States (where I live) to somewhere else (Canada) - tried to pair and it worked!

I had the same issue with my Apple Watch serials 5 and finally fixed it by the guide here: wipelock.com/phone-tips/apple-watch-unable-check-update/

[2021] Top 10 Solutions for Apple Watch Unable to Check for Update (wipelock.com)

What I did to fix mine (after resetting my phone still gave me the error code), I took my watch off the charger, turned it off, then just set it back on the charger. After it came back to the setup screen, I paired it again and it started updating. Not sure if this will help for everyone, but that's what did it for me.

Changing region from United States to Canada worked for me after trying all the other options. Strange that Apple hasn't fixed this bug with a known issue that so many experience.

After trying all the suggestions, the last one I read was about low power mode. Turned low power mode off and instantly allowed the update to begin !!

Put the watch on, and unlock it. Then check for update.....

I tried everything here. And the only thing that worked was changing my Region from US to Canada. The Update started as soon as I did this.

I tried everything. Reseted the watch several times as described above. Restored the iphone to factory defaults several times (a brand new phone, i had no data to lose). Reseted the wifi network in my house. Tried with my neighbors wifi network. More than 5 hours of trying dozens of solutions. Nothing.
Finilly i changed the region and the language on the phone (i live in Spain, changed it to English and region Canada). I couldn't freaking beleive it, it started updating right away. So simple and so weird.

This has just worked for me and my Apple Watch series 3.
Updated the software using a old iPhone 6 watch app that had not been updated I think it had iOS 7 .Then turned that phone off.I then paired as normal with my iPhone 8 iOS 14 watch app and it worked I don’t know how or why but I’m happy.Good luck

I had this issue too where the hard reset did not help. I then went into settings on my watch and was able to initiate the download form there. You will be prompted to accept terms and conditions on your phone. From there you just follow the normal instructions.

Following steps really helped me in fixing this issue. Thank you for posting this solution.

Hard reset apple watch > when the apple logo shows hold down the button next to the crown and hold for 30 seconds > select erase all settings and content.
After watch resets > power down the watch do not hard reset, move the power slider to the right you might have to put in your wrist to do that and then put it back on the charger.
On your iPhone sign out of iCloud completely > go to settings > general > scroll down > shut down iphone (do not hard reset)
Power up Watch and then your iPhone > sign into iCloud/AppleID
Start the pairing process > it should say your watch is now paired > select update > it will give you the update error again saying no internet but let it sit for a minute > boom it will start updating the watch. Headache is GONE hopefully!
Hope this works for everyone because after trying everything these are the steps that I took you might have to try a few times but mine worked the very first try.

I found another way to fix this was to change my wifi from a 5 GHz to a 2.4 GHz network.

Sadly the suggestions here have not fixed this for me. I have a brand new iPhone 12 mini, trying to pair with an Apple Watch Series 1. Hard reseting both iPhone and watch results in the same "Unable to check for update" error message loop. I have internet access, and have confirmed all the other sanity checks from the Watch support page.

Can someone from Apple please escalate this case to the development team, pretty please! :) thanks

I've also tried changing the region to Canada, on both iPhone and Watch, but I still see the same error loop.