"Connecting your Apple Watch. This may take a moment" stuck.

An update: I was getting the same issue previously that it is up to date with 5.2.6, when I knew the required update was 6.2.1. Somehow after multiple tries it worked and I upgraded to 6.2.1. Initially it did show 1 day to update but was completed within a few hours. After that, was able to pair the watch to the phone successfully!

Well I grabbed an old iPhone that’s running iOS 12 and it paired without problems. It wouldn’t let me update the watch to watchOS 6 cuz it says my iPhone first needed update but my old iPhone only goes to iOS 12. So I reset the watch and I’ll try pairing again.

So I did get the watch to finally sync... I’ll list out what I did:

Tried to sync a new series 3 watch with a new iPhone 11, got stuck in the loop of “connecting to watch.” I tried everything I could think of to get outta the loop but it never got passed that.

I happened to have an old iPhone 6 that’s updated to iOS 12 which is the most up to date for that phone, the watch had

no issues syncing to that. So I then factory reset the watch and tried syncing to my iPhone 11 again, however, this time I was not at home and was just on 5gE. The watch finally got past the connecting step and to the updating section on my phone but since I wasn't on WiFi it told me I had to connect to WiFi to continue... so when I got home I connected to WiFi and tried again, SAME CONNECTING TO WATCH LOOP. I was furious... but then I reset the watch and turned WiFi off on my phone and tried syncing the watch, it got right past connecting and onto the update again and told me to connect to WiFi. This time since I was able to switch to WiFi immediately and didn’t have to back outta the app and reset the connection, it started downloading. It took several hours (initially quoted the 1-2 days but was done in prolly 2-3 hours). After it updated it connected and I haven’t had any issues since. Completely ridiculous.

If you don’t have an old iPhone laying around, I would definitely try syncing it off of WiFi and if it works then kick the WiFi back on when it tells you to connect to WiFi to continue the update.

I had the same thing happen to me with my series 3 apple watch. It was working fine and then the update came out and just like everyone else says it keeps getting stuck saying "connecting your apple watch" regardless if I try to set up the update or pair it as a new apple watch. Nothing works. I spent over an hour on the phone with customer support and nothing worked. They were going to have me mail it in to get fixed but a senior tech support got on the phone and told me they wouldn't do that and I have to find a local shop that fixes it. Or I can wait until the Apple stores reopen (closed from COVID-19) to have someone check it out there. It's 2 years old so it's out of warranty. SO annoying!

Wow! That actually worked... it never asked me to turn back on my wifi.

i tried all day today- the first time the update took 2 hours. It was stuck on “installing” for a good 30 minutes so i closed the app.

I tried to do it again but it took me back to square one- so i had to install the software again. That took another 2 hours. It went further than the first time- right where it says “connecting to your apple watch”. Then it was stuck there.

I looked on the internet to find answers and I came to this thread. And what you suggested to do actually worked!

I had my apple watch series 3 paired with my old iphone 6 and now i was trying to pair it with iphone xs.

Moral of the story- just keep on trying. Close the app, and start over. Thats what I did and it worked!

This actually worked for me. I was trying to pair my watch 3 to my iphone 11, and it just hung. Finally, restarted watch and phone and switched off the wifi on my phone. I restarted the pairing process and voila. It works. I did set up my watch as a new apple watch, since it was battling to download the backup. Not sure why.

I managed to sort this issue out yesterday morning with my series 4 after over 2hours of pure frustration and annoyance. The connecting to AW message was displayed on my screen initially for about 30 mins before i realised that something was wrong. I simply tried turning on and off both the watch and my iphone X multiple times but the same message was still stuck on the screen. Then i figured that force holding the screen of the apple watch when it showing the pair with iphone message gives the option to reset the watch so i did and retried not much progress. After doing this i tried updating the ios on the phone (i am using the beta version) this seemed to have been the main issue so after this i tried pairing again, it seemed to have made progress because now it sort of paired and asked me to update the OS on the watch after about 15mins the watch os was updated and it starting setting things up but then said the pairing failed. I then restarted both devices again and watched a video which said to reset network setting on the iphone so i did (and i didnt change anything on iphone, all wifi&bluetooth devices etc were all still there after didnt need to enter passwords or anything) and restarted the phone, then tried again and then it successfully paired the devices and they have both been working perfectly since yesterday.

Essentially try the following things:

-Restart both devices (multiple times)

-Reset watch by force pressing the screen like the 3D touch on the iphone

-Charge both devices moderately or leave on charge

-Ensure IOS is updated !! (IMPORTANT)!!

-Reset the network setting on iphone in setting

Doing these things worked to help pair my series 4 and iphone X (using apples beta software) so it may help

Wife's watch says there's an update. She attempts to update, says software up-to-date, version 5.3.7, stuck on that screen, watch doesn't work. After restarts and fiddling around, including resetting watch to factory settings, gets past that screen, and restoring watch from backup gets to "Connecting your watch . . . " which eventually times out. Several times. Last night she updated her iPhone to latest iOS, and now we're back to being stuck on the "watch software is up-to-date v. 5.3.7" again. Which isn't even the latest version, I don't think. I can't delete the update file from the watch because it's not set up, and I can't find it on her phone.

I try to pair the watch to my iPhone SE. At first I get "can't connect to internet to check for an update." I'm absolutely positively connected to the internet. At some point, I say skip the update, which I thought exited the setup, but it goes to "Connecting your watch..." which I watched for an hour in case there was some intervention required before timing out, and then cancelled it. I tried again, and it checks for the update and says "up-to-date, v. 5.3.7." I updated my phone to latest iOS, and deleted and reinstalled the watch app, and now I'm told that I need to update the watch software, it checks for an update, and can't because I'm not connected to the internet, which I absolutely positively am.

I've deleted and reinstalled the watch app, force-reset the phone and watch, I'm on 2.4GHz WiFi, I reset my network settings, signed out of/back into iCloud. All the tricks.

So at this point I have to take it to an Apple Store, and they aren't open, so my wife is without her watch for several weeks. Maybe I'll get her a Fitbit; mine isn't perfect but at least it isn't a paperweight.

Bottom line, though, is when your update process says that it cannot continue because I am not connected to the internet and I demonstrably am connected to the internet, you've got issues. So what's the deal, Apple?

Hi All,

I got a replacement iPhone 8 because I cracked my old iPhone 8 and my watch connected to it just fine. I know this is not a feasible solution for many but I was fortunate enough to have this opportunity and it worked.

I have the same problem with my watch series 4 and my Iphone XS.

Apple support told me there is nothing they can do and I have to wait for a new software update. I had this issue before the 13.5.1 update. They are saying since I am out of warranty they cannot fix it. Meanwhile, I did not damage the phone or watch. This is on their end.

They said I may have to wait months for a fix!

I was in the same boat as all of these poor people. I wasted a large chunk of my day trying to get this darn thing to update, although my phone believed my watch was up-to-date with watchOS 3.something. I am now looking at my phone screen downloading watchOS 6.2.6. Hooray!

What I did was turn off Bluetooth and Wi-Fi THROUGH THE SETTINGS APP NOT THROUGH CONTROL CENTER. I was then prompted to turn on Bluetooth when attempting to pair with my watch (expected). Then, however, my phone was able to detect the latest watchOS update instead of thinking it was already up-to-date. I had to turn on Wi-Fi again for the update to continue (you will see text indicating such at the bottom of the update screen). I am not sure what did the trick, so I included everything I did. I hope it works for you too!

I reset my watch and my iPhone, turned off WiFi and tried to begin the pairing process using mobile data. My phone found the correct update and I turned the WiFi on to start download.

i have been trying different things for around 10 day’s but this solution solved it.

this is what's done it for me i think!

similar issue - pairing an old series 3 (stupidly reset it) to a new iPhone 11 - tried EVERYTHING to try and get it to get past the 'checking for update screen'

nothing would work but as soon as i kicked myself off my wifi it worked fine with downloading the update (6.2.6) and now downloading to my watch. has initially quoted 14 hours, but within a few glances it's gone down to 7. hoping this means it will connect okay!

What should be done if that does not fix the problem?

Hello Hyris,

i have the same problem I have never reset it since I bought it as I forgot my password I wanted to reset it and now it’s blocked. It’s stuck at the connecting phase