WatchOS 27 Update Issue

Try this in your watch (not on the phone): go to Settings -> General -> Software Updates -> Install. It might require that you confirm the update on the phone and place the watch on the charger.

There seems to be a glitch in iOS27 that prevents the installation from being started on the phone.

I hope this helps.

My install stopped stopped after "preparing update" completed. I did as suggested above on the watch (not on the phone): go to Settings -> General -> Software Updates -> Install). The install started immediately. Thank you!

**Update**

I updated my phone to the iOS 27. I unpaired the watch and iPhone. I put the watch on the charger and made sure my phone was connected to both wifi and bluetooth. I restarted the process of pairing and updating the watch OS. The process took about an hour, but it worked.

There is no glitch with the watchOS 27 being started on the phone. The issue is that many folks seem to misunderstand that when starting the download from the Watch app on an iPhone, you must enter your passcode on the watch to proceed with the download and installation.

The watch has to be on its charging puck for watchOS to be installed.

Same issue here with a brand new Ultra 4.

• On iPhone 17Pro Watch app stalls on Preparing.
• Then rebooted Ultra 4 and iPhone and used on Ultra: Setting/General/Software Update and update worked fine.

Thanks for the advise

We tested the heck out of watchOS 27 in beta. I had no issues installing it!

The issue is that many folks seem to misunderstand that when starting the download from the Watch app on an iPhone, you must enter your passcode on the watch itself to proceed with the download and installation.

The watch has to be on its charging puck for watchOS to be installed.

If watchOS 27 has downloaded but won’t install, first make sure the Apple Watch is on its charger, above 50% battery, connected to Wi-Fi, and close to the paired iPhone.

Then try:

• Open the Watch app > General > Software Update and check again.
• Restart both the iPhone and Apple Watch.
• If the update is stuck, delete the downloaded update from the Watch app if the option appears, then download it again.
• Make sure the iPhone itself is fully updated.
• Temporarily disable VPN or network-filtering services.

If there is still no Install option, it may be a temporary verification or update-server issue.

More Apple Watch and iPhone troubleshooting guides: https://nexploreinfo.com/how-to-download-and-install-ios-27/

You likely now have a damaged watchOS Update file. You should remove this file and start the Update process fresh. Follow either of the steps in this linked article to remove the file using the watch itself or the Watch App on your iPhone.

https://beebom.com/delete-apple-watch-software-update-file/

Remember that Usage is most likely called Storage on your devices now.

After you have deleted the file, restart both the iPhone and the Watch. Then attempt to update the watch again.

Update your Apple Watch - Apple Support

Your iPhone usually needs to be updated first. The watch needs to be charged to a minimum of 50%. The watch needs to be placed on the charging puck after you have begun the update. The phone and watch need to remain in close proximity until the watch has been completely updated.

If watchOS 27 has downloaded but the Install option is missing from your iPhone, try starting the update directly from your Apple Watch.

1. On your Apple Watch, open Settings > General > Software Update.
2. If the Install option appears, tap it.
3. Place the watch on its charger and ensure the battery is at least 50%.
4. Keep your iPhone nearby, connected to Wi-Fi, and updated to iOS 27.

If the installation still does not start, open the Watch app on your iPhone, go to General > Storage, locate the downloaded update file, and delete it. Then download the update again.

Several users in this discussion have reported success by initiating the installation directly from their Apple Watch.

Apple's official troubleshooting instructions also recommend removing the downloaded update file if installation will not start.

I had the same, until I went into my watch (series 9) and saw it said verifying. When I placed my watch onto the charger, after a little while it started installing.

Had the same problem. Going to settings on the watch and hit install there fixed the problem

El Chavo wrote:

So, the issue has nothing to do with "a glitch in watchOS 27"!

The issue is that folks have not updated their devices to the most recent previous OS before attempting to upgrade to the new OS!

Apple software usually requires that a device is up-to-date, before any attempt to move on to an upgrade of a new OS. In this case, an Watch needs to be updated to 20.6 before upgrading an iPhone to iOS 27 and a watch to watchOS 27.

Yes, a careful reading of Apple's instructions does indicate that the order indicated by El Chavo has to be followed. That said, it seems that Apple's process maybe should be more forgiving of being behind on the latest version on the watch. For most Apple devices, one can skip over multiple intermediate updates while updating to the latest. However, there are apparently enough fundamental changes in moving to OS 27 for all Apple devices that Apple's documented step by step process needs to be adhered to, as indicated by EL Chavo: both the watch and iPhone need to be on the latest version before first the iPhone is updated to 27 followed by the watch to 27.

bcgav wrote:

Not just updating an Apple Watch to WatchOS 27, updating an Apple Watch that is on WatchOS 26 that is not supported in WatchOS 27 and had a pending WatchOS 26 update downloaded.

Exactly. The latest version of WatchOS 26 has to be downloaded AND INSTALLED before the update to WatchOS27 should be executed. The iPhone also has to be on iOS 27. This is all explained in Apple's guidance.

For those having this issue updating watchOS 26 on iOS 27, see this thread for a solution:

Apple watches cannot be updated to watchO… - Apple Community

@El Chavo - FYI apparently there is a bug where a watch that has downloaded but hasn't yet installed a pending watchOS 26 update that is paired to an iPhone that gets upgraded to iOS 27 prior to the update, the watch ends up getting stuck where the update continues to fail.

I am setting up a brand new iwatch 11. It wouldn’t install until I updated my iPhone 13 mini to iOS 27. That worked. The Iwatch 11 has been “installing” now for a day, with nothing showing in the watch screen except “46mm aluminium case”. Obviously I can’t go to the watch settings. Any ideas? Garmin perhaps?

If you will recall, Apple released public announcements that were carried in most tech mags at the release of 26.6, that OS 26.6 prepared Apple devices for the upgrade to OS 27.

https://duckduckgo.com/?q=watchOS+26.6+prepares+Apple+hardware+for+OS+27&t=brave&ia=web

I’m currently experiencing the same issue. I have a brand new watch 10 series and I’ve tried installing with no success and disconnecting and resetting several times. I’ve also updated my phone to the latest OS.

***Update***

Regarding the issue of iOS27 and pairing/installing a brand new iWatch 11, (stuck on “installing” with no action on the iwatch)… I restarted both the iphone 13 and the iWatch 11 (which reset to factory settings) and kept the IW on its charger, started the process again by pairing the new IW, at which point it asked if I wanted up update to iOS27 or continue without updating. I chose that option - don’t update - and everything went as smoothly as an Apple install should.

So yes, I essentially switched it off and on again!

I have an iWatch series 8. Updated my iPhone to IOS27. This disrupted the connection between my iPhone and watch. I tried several times to update the IOS for the watch to 26.6 I but kept getting error messages. I have tried going via the iWatch directly. Similar to one of the tips in this thread. Still no luck. I have now reset my iWatch by disconnecting it and trying to reset it. Now I can’t reconnect my iWatch because it needs me to update the software when reconnecting. I get the same error message. I can’t use my watch now. I’ve tried several times to reconnect it but it’s not having it. Effectively, my watch is bricked. I’ve tried going into storage on my iPhone to see if I can delete the update in the Watch app. No

such luck.

Appreciate your feedback, but when I tried to download the WatchOS 27 via the Watch app on my iPhone, I did enter my passcode on my Watch and my Watch and iPhone were both on their charging stations. The message I was getting on my phone was "verifying" then "installing" but the update did not go through and I received an error message.

I have a similar problem - watch is SE 2nd gen, iPhone 17 Pro running iOS 27. My watch stopped interacting with my phone - no alarms or text message notifications - after the iOS 27 update. I tried updating the watch, but the update failed every time (and yes, I entered my passcode). I tried deleting the watch app (to ideally re-download the update), unpairing and resetting the watch, and starting with again after redownloading the watch app. I couldn't even start to use the watch without updating the watch OS, which failed every time. I went through this process at least 5 times (the watch was on the charger every time, solid wifi, etc), and now the phone doesn't even sense the watch - it's a complete brick.

I did reset my Iwatch it’s a 9 series and now I am trying to pair with my device it says about 2 hours remaining later it says paused even after keeping my watch in charge mode for hours and my WiFi is connected and Bluetooth is on.

Sorry El Chaco - you are wrong. I would consider myself an advanced user - know what I’m doing - help solve hardware and software issues for others, …

There’s a problem with iOS for Apple Watch software update with iOS 27.

Maybe be a little more open to information in the future. Ask questions, you know - think a little.

Just because it worked for you in Beta, doesn’t mean it’s going to work for everyone else. You tested the Beta with your configuration - you aren’t considering the dozens of other configurations that others have.

So, the issue has nothing to do with "a glitch in watchOS 27"!

The issue is that folks have not updated their devices to the most recent previous OS before attempting to upgrade to the new OS!

Apple software usually requires that a device is up-to-date, before any attempt to move on to an upgrade of a new OS. In this case, an Watch needs to be updated to 20.6 before upgrading an iPhone to iOS 27 and a watch to watchOS 27.

I was able to update my iPhone to 27.0.1 but unable to update my Ultra watch. I've tried updating the watch through the watch app and my phone and still nothing. When I click install the verifying appears and then I get "an error occurred while updating please use the watch app to continue". It's a continuous loop between the phone and watch app. I uninstalled and reset the watch but I'm unable to pair the watch again due to the software update.

This doesn't work for me, there simply is no "Install" button anywhere.

I am unable to update my AW.

Thanks, this helped a lot! I hope that Apple does more beta testing before putting out any more software updates to make sure they upload correctly. :-)

Same issue. Watch is effectively bricked.

No go

Apple Ultra Series3

Same, having issues. No watch faces. Account pair issues.

I'm pretty sure that the hundreds of beta testers cover about any configuration of watch and phone available.

No one reported glitches installing the public release.

Apple Watch 6, update to watchOS 26 keeps failing after upgrade to iOS27 on iPhone. Watch unpaired then reset, went through pairing process, prompted to install update, then update keeps failing.

Not just updating an Apple Watch to WatchOS 27, updating an Apple Watch that is on WatchOS 26 that is not supported in WatchOS 27 and had a pending WatchOS 26 update downloaded.

I tried the above didn’t work after third attempt I reset watch and still cannot install update. Looks like I’m going to try a different brand

Tooks forever of installing the new version and i can’t open my watch app coz of this 😩 Im so stress now!!