Issues setting up/restoring older Apple Watches on iOS 13.4

I had this exact same problem with a brand new Apple Watch series 2. I phoned Apple support. Tier 1 support couldn’t solve it but Tier 2 support got it solved.

Here are the steps we did which worked:

1. Tap “Cancel” on the watch update screen where it says the watch is already up to date and tap to reset and unpair the watch. Let this process complete.
2. Force restart your iPhone. (Different models have button combinations to force restart. See here: https://support.apple.com/en-gb/guide/iphone/iph8903c3ee6/ios)
3. Force restart your Apple Watch (hold down the Digital Crown and the side button at the same time. Keep holding them down until the Apple start up logo appears).
4. Now open Apple Watch app on your iPhone to pair the watch. Instead of using the camera method tap the text near the bottom of the screen that says “setup manually”. Follow the process through according to the prompts on the phone. When it then gets to the update software screen it should now identify the correct WatchOS version and download that.
5. You’ll need your watch on the charger to complete the update (and the update took several hours to download but finally got there).
6. After that, if you’ve had a watch connected to the phone before you’ll be given an option to restore a backup or set it up as a new watch.

This worked for me. Hopefully it will work for others too.

If you’re still stuck you can phone Apple Support. I was pleasantly surprised at how good their support was and how quickly they helped get things fixed.

Hi ,

I had the exact same issue while trying to pair Series 3 watch with iOS 13.4. Below 2 things helped me.

1. In your iPhone settings, reset your Network Settings .
2. Make sure iPhone and watch are on the same WIFI network.

After this , if you try to pair your watch again , it will download the latest 6.2.6 and the pairing works.

Hope this helps.

This is becoming a bigger problem every day,here is one solution from another forum;

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 watch OS I unpaired the watch from the ios12 phone and then was able to pair it with any iPhone running iOS 13.

I have this same issue. My Series 3 screen broke and I wanted to get my Series 1 back working for a while before I bought a new one. I'm not even sure what WatchOS version is on the watch. But when I try to update the WatchOS during the pairing process it asks me to update my iPhone iOS to the latest to continue. But my iOS is already at the latest version for my iPhone 7 ( 13.4.1 iOS). I've searched everywhere for a fix, but this is the only post I've found so far that matches my issue exactly. Hopefully Apple can fix this with an update.

Any update on this issue? Are you watches all MIA since you all posted here? MY watch wants to pair but my iphone wants to update then says it's up-to-date, just like OP's. This is frustrating to say the least.

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 on ios12 and can confirm that it works 100%.

Hi all, I had the same exact problem. An unwanted 1 or 2 Apple Watch was passed on to me and I couldn’t break through the storage update stage. After reading this chain I grabbed my boyfriends phone (iOS 12) and went through the same process and am now currently updating the Apple Watch, further than I ever got on my phone with iOS 13. The best option for now is to try and use a device that hasn’t yet got iOS 13, like mentioned above. Good luck!

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.

In case I’ve missed a post this solution is the one that requires you to know someone with an OS of 12 on their phone and will allow you to sync your watch with their phone firstly?

or is there an official Apple solution.

I have the same issue,

Old setup:

IP6 12.4.6 and Watch(3) 5.4.1

Just took delivery of a new SE 2020.

After unpairing the old IP6 and my watch the new phone asked to pair with the rest watch.

It pairs and detects that a software update is needed.

After selecting to update i get :

' Unable to check for update ' Checking for a software update failed because you are not connected to the internet'

Followed all the guides to repair with the old IP6 and that works, updated the watch to the latest version (5.4.1) and all is well.

Unpair again, and try to pair to the new SE, and still get the same issue.

Apple support has suggested I send the watch in.

Would clearly think this is more a software issue than a hardware issue so at this moment it looks like the only option is to send the watch in for them to update the watch manually.

Joy...

Same issues.

Iphone7 on ios 13.5.1 and Apple watch 3 - can't pair. Errors either say: 1) Not connected to internet 2) Already up to date on with watchOS 5.3.7 or 3) Unable to check for update. This is clearly a bug with recent iOS versions as the watch will pair with an iphone on iOS 12. I was also told by Apple support to send in my watch for repair (over $200 charge) but this is clearly a software problem so I refused.

APPLE PLEASE FIX THIS BUG!

I had this same issue for days with my watch series 3 and iPhone XS. I then tried to pairing it with my husband's phone which is also an iPhone XS. It looked like it was going to work, but then got stuck again in a different step, so I just stopped the pairing again. After this, I tried again on my phone to see if a miracle would make it work and it did. The new watchOS was downloaded and then the watch was paired.

So if you can, get someone to let you use their iPhone, and try to pair it.

Minor update,

Paired it again with my old 6, where it suggested an upgrade to the watch and after finishing it ran 5.3.7.

I reset the watch and tried to pair it to the SE but no luck still same old issues.

Weekend came and I just put things to the side, and tried again yesterday.

The watch pairs, and updates to 6.

Hello,

my watch will not do the update. The screen does the thinking icon. Also my iPhone X will not let me access the Files or pages I had save with the iCloud Drive. It tells me encrypted files and to authenticate. I have no clue wtf happened to my devices but after this update they are whacky.