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

Hi. I am pairing my Apple Watch Series 5 to my iPhone running ios 14. The pairing is successful but unable to proceed with the set up because an update is needed to be downloaded first. I updated the os for watch but I keep on getting “Unable to Check for Update - Checking for a software update failed because you are not connected to the internet”. I am definitely connected to the internet.

Watch was reset to factory defaults and I am now pairing it as a new device but it fails due to the issue mentioned above.
Answered by heisenbert in 633607022
Hard resetting iPhone fixed this issue.

Steps are:
  1. Press Volume Up and let go.

  2. Press Volume Down and let go.

  3. Press and hold the side button.

Note: This does not wipe any data from your phone

I was facing same issue. Trying to connect Watch after 1 year and getting the error. Tried everything nothing worked. Finally figured out a way to update.

It seems like my watch was running on WatchOS 6 and Iphone 12 is not supporting next update of Watch OS 6, i.e. watchOS 8.8. I had to borrow a iphone 7 and pair my watch and updated it to version 8.8 then unpaired from the borrowed mobile and paired with my iPhone 12 Pro. This time it got updated to WatchOS 10 without any issue.

Posting as this may be useful for others.

What worked for me:

  1. Hard restarting my iPhone 11 Pro Max (Volume up button/Volume down button/press and hold Side Button until I see the Apple logo)
  2. Hard restarting my replacement Series 5 Watch (hold Digital Crown and Side Button until I see Apple logo)
  3. Turning on low power mode on my iPhone (I am not sure this matters, but another user in this forum wrote that it worked, so I thought, "why not?")
  4. Trying to pair again by holding iPhone in proximity of Watch and crossing my fingers.

The new watchOS started to download to the Watch via my iPhone.

Thanks!

I had the same issue with a watch I hadn't used for a while and needed to pair to my new phone. I followed the steps dogr suggested (restart phone and watch, low power mode on phone) and that worked for me.

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