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

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

Hello hyris,

Thank you for using Apple Support Communities. It's my understanding that your Apple Watch becomes unresponsive when trying to connect with your iPhone 11 Pro. You've come to the right place! I'm happy to help.

If you haven't already, restart your Apple Watch and iPhone.

How to restart your Apple Watch

Restart your iPhone

Next, make sure that your iPhone has Bluetooth turned on and is connected to Wi-Fi or a cellular network. Then use the steps in the following resource to set up your Apple Watch:

Set up your Apple Watch

Have a nice day!

Hello hyris,

Thank you for using Apple Support Communities. It's my understanding that your Apple Watch becomes unresponsive when trying to connect with your iPhone 11 Pro. You've come to the right place! I'm happy to help.

If you haven't already, restart your Apple Watch and iPhone.

How to restart your Apple Watch

Restart your iPhone

Next, make sure that your iPhone has Bluetooth turned on and is connected to Wi-Fi or a cellular network. Then use the steps in the following resource to set up your Apple Watch:

Set up your Apple Watch

Have a nice day!

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.

I did a few steps and it worked for me. It might work for someone else:

• Erase the Apple Watch;
• Update the Apple Watch to the latest possible version;
• Reset the Apple Watch;
• Reset the iPhone;
• Keep both the Apple Watch and the iPhone charging;
• Do the pair setup on a cellular network.

Following all these steps I were able to pair my Apple Watch successfully.

They are not telling the truth. They cannot resolve why this is happening and they don’t guarantee that it will fixed. What a load of bs if they knew this was an issue they should address appropriately and give us some type of discount or to trade in these painless Apple Watch. All the above “fixes” are bs and will not work.

They are not telling the truth. They cannot resolve why this is happening and they don’t guarantee that it will fixed. What a load of bs if they knew this was an issue they should address appropriately and give us some type of discount or to trade in these painless Apple Watch. All the above “fixes” are bs and will not work.

I am having the same problem. I have a brand new Apple Watch series 4 and keep getting a software update failed notice. I bright it back to were I purchased and they tried another watch and same failure notice. I spoke with Apple this morning and they were no help. So I don’t know what to do. I may just return and not get another watch. This is ridiculous.

Experiencing exactly the same as you, fernand272. Brand new Apple Watch series 4, trying to pair to my iPhone Xs and software update failed immediately. Nothing seems to work... indeed a nasty bug escaped.

Same thing here. Purchased an Apple Watch series 4 and can't finish the pairing because it keeps failing on the update. Spoke to Apple and they suggested trying another watch but from reading comments it sounds like others have tried that and had no luck!

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.

Same issue. Did a full wipe of my AW Series 3 because update kept failing. Now cannot update from previous back up or set up AW as new. "Connecting you apple watch....." stuck with that message !! Iphone OS is latest. AW - not sure of previous version. But trying to get to WatchOS 6.1.1

I'm now getting watchOS 5.3.4 in the pairing process (was 6.1.1 all weekend) , but same result: either "connecting your AW..." stuck situation when I choose not to make the update or "software update failed..." error when I choose the update way, and back to square one. Yet... I get stories of people with no problems at all. Strange indeed.

I am having same issue connecting my iwatch series 3 connecting to iPhone after iPhone upgraded to latest iOS. Tried everything including restarting my iwatch and iPhone many times but issue is not resolved. Wasted over half of my day today. Very frustrating!!!

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