"watchOS 5.3.8 your software is up to date"

Just got off with apple support -- what worked for me was taking the watch to a coffee shop to pair. Apparently the watch can't connect to 5G WiFi networks, but 2G works fine for the software update (and most public WiFi is 2G). FYI it did take over an hour to update.

I have wasted about 6 hours trying every solution posted on the internet.

Don't be like me, instead do 'this':

1. Find an older model iPhone (eg iPhone 6) that is running a 12.something update (13.something's don't work).
2. Pair to this older phone
3. Once paired, update the Apple Watch using the older iPhone
4. Once updated, unpair from the old iPhone
5. re-Pair to your newer iPhone (in my case an 8).
6. Complain to Apple. This has been such an annoying exercise

Disconnecting from WiFi and initiating the watchOS upgrade from my phone’s Cellular connection worked. It started downloading the latest version 7.0.1 and then asked me to reconnect to WiFi which completed the upgrade, pairing and setup of the watch.

For anyone still looking for solution to this, just tried this today with the new iPhone with iOS 14.1.

1. delete the existing watch app.
2. download the watch app from the App Store.
3. reset your watch by holding the watch power button. It will give you a warning that this will factory reset.
4. once reset is done, try pairing and it should now able to download the update to the watch; version 6.2.8. Warning, this took me 3 hours after all is said and done. Install warning said that it will only start if watch is more than 50% charge, so might want to keep phone and watch on charge.

Good luck!

I tried EVERYTHING I found online and nothing worked, then (after a call to Apple) they said to reset Network Settings on my iPhone and then reconnect the WiFi. IT WORKED!!! It then let me download the 6.x.x watch IOS.

I hope this helps with someone else!

After spending about 4 frustrating hours, trying everything I could find on these posts, I switched my WIFI from 5ghz mesh network to 2.4ghz and the watchOS 6.2.8 finally started downloading. How frustrating but glad I finally figured out the problem. Hope this helps others that have the same problem. This worked on IOS 14 beta.

Guys I've been having the same issue for months and i just found a solution...

1: delete watch app

2: restart apple watch and iphone

3: redownload watch app

4: pair watch and it will update successfully.

btw im using ios 14.0.1 iphone 6s plus and apple watch series 1 but you can try with ur devices as well

I ran into the exact same problem with the iPhone Xs on iOS 14.1 and the iPhone SE on iOS 14.0.1 attempting to pair with an apple watch generation 2.

Once I upgraded the iPhone SE to 14.1 I was able to upgrade the apple watch using the iPhone SE on iOS 14.1 to the watchOS 7.0.3. After the apple watch gen 2 was upgraded to 7.0.3, I was able to pair the watch to the iPhone Xs using iOS 14.1

It worked for me when I reset network settings.

Thank you ddday, it worked with my watch! (I cancelled appointment with Apple)

I connected iPhone to 2G, reset the watch and it worked! Updated to 7.0.1.

I went to the Apple store for support for this exact issue; a brand new replacement Watch came with 5.3.8 against iPhone 11 with 13.6. Deleting the Watch app, then reinstalling it, enabled me to move to the next step.

This info was like diamond to me.

What worked for me was:

1. Hold the Digital Crown and select reset your Apple Watch.
2. Connect your iPhone on a 2G WiFi
3. Try again

Thanks, your post sorted my problem, I switched my phone to 2g on my router and the watch updated and is working now.

Hi all,

I tried to use an 11 pro to update the series 4 last night. It finally worked!!!

So, maybe give it a go with different generation iphone.

Good luck

Exactly the same issue . Apple watch Series 4 + iphone X IOS 13.5.1 stuck at watchOS 5.3.8 your software is up to date.

Not sure whether NEW IOS 13.6 can fix the issue or not .

Need advice from APPLE support.