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Apple Watch Update Unsuccessful

When I attempt to pair my Apple Watch (Series 3) to my iPhone X for the first time it says I must update my WatchOS software first. When I press “Update Now” it takes ~30 seconds to activate the watch then it checks for updates. After a good 15-30 seconds of checking for updates, it says “Unable to Check for Update” because it says my phone isn’t connected to the internet. I can confirm my phone is connected to the internet. I got it to download WatchOS 5.3.7 (I am aware this is definitely not the latest version of WatchOS but the only version that came up to install) so I installed it. I then tried pairing again once it was done and it proceeded to show the same error while checking for updates. This is a replacement watch I got from Apple after my last one’s screen broke (defect) and they replaced the whole unit. The last watch didn’t have any issues when I paired it. I’m on iOS version 13.5.1. Any ideas? Thanks :)

Apple Watch Series 3, watchOS 6

Posted on Jun 4, 2020 11:05 PM

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Question marked as Top-ranking reply

Posted on Jun 7, 2020 12:32 AM

Apple support tried to contact me a few times yesterday, but unfortunately I wasn't able to answer. Assuming they had good news for me (and for us), I decided to give it another try and start the pairing process again. For my surprise, after more than one hour, even without any iOS update, I was finally able to pair my phone with the watch.


My iOS version is 13.5.1 while the watch is running 6.2.6 now (released in 1 Jun 2020 according to Apple's support website Apple security updates - Apple Support).

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Question marked as Top-ranking reply

Jun 7, 2020 12:32 AM in response to tanner170

Apple support tried to contact me a few times yesterday, but unfortunately I wasn't able to answer. Assuming they had good news for me (and for us), I decided to give it another try and start the pairing process again. For my surprise, after more than one hour, even without any iOS update, I was finally able to pair my phone with the watch.


My iOS version is 13.5.1 while the watch is running 6.2.6 now (released in 1 Jun 2020 according to Apple's support website Apple security updates - Apple Support).

Apple Watch Update Unsuccessful

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