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

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!

UPDATE to this post: https://discussions.apple.com/thread/250998383?answerId=252785388022#252785388022

Retried the update on my wife's phone again this morning. Went to check for an update: "Not connected to the internet". Tried again and got the Watch OS update screen for version 6-something. It had been telling us it was up-to-date at 5.3.7. Took 2 or 3 hours to complete the process, but watch is functioning again.

The only thing we did different is bring the watch and phone downstairs closer to the WiFi. That did not help trying to pair it to my phone -- all those failures were done downstairs, so it seems unlikely. I think a more likely suspect is glitchy Apple servers. We didn't really change anything else, so all I can suggest is to keep trying.

Update the iPhone to latest version if the OS , it will work.

I had the same issue. My updates were fairly quick compared to other times I've updated which took quite a bit longer. I say try to update both and if one of them doesn't have an update, restart the phone like I did.

I brought mine into the Apple store and they sent it out to get a new software update. I should get it back in a week. Apparently it’s the only way to get it fixed.

Hey all. I had this is same issue today. These instructions worked for me: https://www.google.com.au/amp/s/www.ikream.com/how-to-fix-an-apple-watch-4-that-wont-update-apple-watchos-update-error-34338/amp

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!

Spoke to Apple again today and they said engineers are aware of the issue and that there should be a fix in a few days. So fingers crossed!

Don’t give up. Disconnect, unplug, delete. Turn off WiFi. Then start again.

it worked for me after 10 days of trying

I’m having this issue with a series 3 cellular model as well, I went as far as wiping my phone completely and trying again. Started with the software update failed. Then I reset the watch and tried again. Tried setting up as a new Apple Watch and skipping the software update, sits there “connecting to your Apple Watch. This may take a moment.” Never finishes. Wish I came across this post before I spent the last 4 hours of my life trying to resolve! Hopefully they figure out to resolve this issue soon.

Literally keep having this same issue. It resent my Apple Watch without me knowing and I can’t even wear it now. My update continues to fail and when i try to repair without it, it gets stuck too...I have. Spent countless hours trying to fix this...if it doesn’t get fixed I will have to switch to another product...ughh

It seems I have experienced all of these related issues with my brand new Apple Watch series 4. I have reset/restarted my watch and phone several times, tried various networks, and made sure to keep my phone and watch plugged into a charger. I also noticed that each time I reset the watch and iPhone, it would switch between software updates 5.3.4 and 6.1.1......After my first call with Apple, the “advisor” told me it was a server related issue. I called back the next day to see if the issue was fixed, and the other “advisor” has no idea what server issue I was referring to. I set up an appt at the Apple store based upon the comments in this feed. For sh*** and giggles I decided to try one more time(my 15-20th try) about hour before my appt. Of course, for no reason at all, it decided to download the update. Unbelievable... I don’t even know who to blame.

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.

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