Unable to pair Apple Watch with iPhone after OS update

Try this;

Press and hold both the side button and Digital Crown for about 10 seconds, then release both buttons when you see the Apple logo.Wait a few seconds, then hold down just the side button for about 20 seconds until the “erase all settings” prompt shows up on the screen, then tap on it, then tap on the green check button.

Then start again.

I had the same issue with Series 1 and iPhone X on 13.4.

I haven't used my series 1 for a while (currently using series 5) and when I tried using my series 1 I faced the same issue in which it was stuck on 5.3.6.

Contacted Apple who suggested trying on another iPhone, which did not work. Then suggested updating my iPhone to 13.4.1 which I did, along with trying the suggestion from fireyjack and this seemed to do the trick and allowed me to update my watch to OS 6.2

The update did take 3 hours though.

Hi, nc94

I do have the same problem. After updating my iPhone7 to iOS 13.4.1, it told me that I should update my AW series2 too. I did that but I stuck in that loop that it didn't go any further.

I've tried lots of things, but nothing works.

My AW series2 has the "WatchOS 5.3.6" but it cannot be paired with my iPhone.

Dang, I shouldn't have updated my iPhone in the first place....

Anyone has any solution?

This is becoming a bigger problem every day especially with 1st generation watches,ios13 doesn't seem to like watches with watchos5 or below,here is one proven solution from another forum;

Quote;

I found a friend, who was on iOS 12 and used his iPhone to pair. Before pairing it asked to upgrade the watch OS (iOS 13 didn't offer this option). After I upgraded the watchos I unpaired the watch from the ios12 phone and then was able to pair it with any iPhone running iOS 13.

I tried this myself with an old watch and phone that I have and can confirm that it works 100%.

Thanks. I think you are right. Had this issue when I first bought my Apple Watch 6 months ago and had a 6s iPhone. They sent me a box and I sent the Watch back to them and they put in anew OS. Sent it back. That was fine for 6 months til I got the new iPhone SE 2020 last week with a OS of 13 and something. So here we go again. I am sending it back to them. The watch has a lot of warranties on it, so at no cost to me. I hope this helps. Thanks for your information!

Tried to update with iphone6 with ios 12. It says that 5.3.7 is the update. Same erros: can not verify update, phone is not connected to internet.

same thing with my iphone XS. Latest update is now 6.2.5. Can not verify update, no internet.

so annoying. Can ’t use my watch at all. Watch is now running 5.3 and it is model 3 (old).

any ideas?

I'm having this issue with an Apple Watch series 4 bough new from Amazon this week, after talking to Apple support over the phone they said it will have to be sent in to them for repair so that the technicians can update it to watchOS6 for me, however I will be returning it to Amazon as I know the only way that the repair centre can update the OS is to open the watch up.  I don't want a brand new watch that has been split open after only being a few days old.

@fieryjack Finally is able to get my iWatch updated! The iWatch 4 was paired at some point with my iPhone then I decided to reset it and unpaired it. After that I can only get to the screen that says your iWatch is up to date with watchOS 5.x. iPhone was not detecting that the latest is 6.x. Spoke with Apple support and they created a repair ticket for me send the iWatch in. After erasing all content I was able to pair and install watchOS 6.x. Saved me a bunch of time sending the iWatch for repair. Thank you!!!

i had the same issue with my brand new AW series 4. My Iphone was on IOS 13.5.

After numerous attempts to update my AW to Watch OS 6, it was always saying that the software was up to date. Which is not correct.

Then,I decided to restore my phone to factory settings. same issue.

After trying a bunch of times, the Apple watch App finally decided to show an available update for Watch OS 6.2.5.

I don't know if this is a glitch or something else but it seems like perseverance pays off in the end.

I’ve had this on my watch in twice once when I bought it so that the OS system could match the one on my phone and then just recently when I got a new phone. I just got my watch back and everything’s fine. I wouldn’t worry about it. The watch has been great I’m not sure if I’ve gotten two or three different ones or if it’s all the same watch but each one of them has worked

I have an Iphone 6 running IOS 12.4.7 and the latest it will update my watch to is atchOS 5.3.7. I can pair, wipe, unpair and pair again on the iPhone 6 with no problems. The issue is when I attempt to pair it and update it on my new iPhone SE 2020 on IOS 13.5.1. The watch pairs but then gets stuck on the update saying that its unable to connect to the internet. I tried everything thinking it could be a network issue, I tried a VPN, resetting the network settings, restarting my router and even on cellular data, no luck. I don't see anything anywhere on my iPhone 6 or my iPhone SE where is says "WatchOS 6 Avaliable". It does however say on my iPhone 6 that to update the WatchOS any further, I must update my iPhone 6's IOS version but, there is no further IOS updates for the iPhone 6.

UPDATE: I got it to start downloading and installing WatchOS 6.2.3! You need something like an iPhone 6S on any version of IOS 13 that is below 13.5! Any apple device that is running IOS 13.4.X will work! If this helped you, please mark it as helpful, the apple rep I talked to said this is a common problem and they do not know how to fix it.

UPDATE 2: You can't setup the iWatch with the IOS 13.4.X device. Once you see the screen say "connecting to apple watch" just hit "cancel" let it do a factory wipe. Then pair on the IOS 13.5+ device and setup from there!

I think that it was already solved try to link and out of nowhere came the update to 6.2.6 I proceeded to install it and without problems I already have my apple watch series 1 linked with my iphone 11 with ios 13.5.1

****, same here. Watch Series 2 stainless steel. Not ablt to pair with 11 Pro Max running 13.5.1

tried to set up on s6, no issues. Watch is running 5.3.7

as per above tried to set up on iphone SE, the old one running 13.3.1 and got a message from watch up that to update watch os i have to update my phone. ****.