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 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!

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.

Apple will fix this problem for free! I have an iPhone XR and was having trouble pairing it to a brand new series 2 watch. When trying to pair on my phone it wouldn’t read the animation or provide the number code to pair manually. I then tried on an iPhone 6 and was able to get to the point of seeing it needed an update but not being able to update it. I sent it into Apple and they sent me a new refurbished watch and it has been working ever since!

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.

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.

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...

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.

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 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.

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.

Same issue, i tried to pair and update iwatch series 1, my iphone has ios 12 and other iphone ios 11, and also i tried on 13.6,

watch has os 3.1, nothing worked, same problem as in the message at the beginning of this thread. So how can we update our old watches and pair when they are restored on factory settings and this problem appears?! i’ll take mine to service :( hoping they have some solution

I finally gave up and purchased a new watch (needed/wanted a new one anyway). After pairing the new watch 5 to my iPhone XR/iOS13, I gave my old watch 2 (the one that wouldn't work on my iPhone XR/iOS13) to my daughter and low and behold, it paired with her newer iPhone 11/iOS13 just fine (even though I tried pairing old watch 2 with other older iPhones in our house running iOS versions older than 13). Evidently, somehow you have to remove the watch from being paired to your phone (or try pairing someone else's watch with your phone?), then re-pair your watch. ??