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This is one of the things that are hit or miss.. maybe someone can chime in.. but sometimes when I screen shot from the watch sometimes it shows up on my phone and sometimes not.
 
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Mine stopped showing up regularly after one of the 11.2 betas. It still doesn’t appear to be fixed in the final 11.2.

The only way for me to get watch screenshots in Photos now is to restart the watch. After doing that prior screenshots will be uploaded to Photo and the first new one I take will also be uploaded. Then it stops again until I restart.
 
Mine stopped showing up regularly after one of the 11.2 betas. It still doesn’t appear to be fixed in the final 11.2.

The only way for me to get watch screenshots in Photos now is to restart the watch. After doing that prior screenshots will be uploaded to Photo and the first new one I take will also be uploaded. Then it stops again until I restart.
This.
 
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Never had any problem with previous watchOS versions. Posting with this annoying problem after 11.2 update, grateful to see a temporary fix and to subscribe to this thread. Thanks for the fix, getting us thru until an update comes to permanently correct the problem. (AW9)
 
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Has been an issue with my new Series 10 after updating to 11.2. Screenshots taken on the watch will sync only after restarting both watch and iPhone. However this will only sync the older screenshots. All screenshots taken after restart will still not be visible. Restarting both again will only fix this.

Hopefully the issue will get fixed with 11.3 and iOS 18.3.
 
Mine started doing this after the 11.2 update on my AW8. Screenshots don’t sync to my iPhone till after I reboot my watch. When I reboot my watch, all the saved screenshots then sync to my phone, once. Then not again till I reboot again.

This is a pain in the butt, because I use this feature a lot to capture what time things happened.
 
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Every update is a crap shoot for what’s going to break, that worked before. You never know, you just have to go with it.
 
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Or bide your time until known issues are fixed or until you need something that's offered in the update. In my case, I held off for weeks, skipping watchOS 11 altogether until I got nagged the day before New Year's Eve to update AW9 after updating iPhone 15 Pro Max to iOS 18 (I waited a really long time for that one, too.) But you're right about the crap shoot, sad to say.
 
Withstanding the fact that it's virtually impossible for me to do the dual-press with my AW6 (2/41 success rate (I've basically beaten teh be-Jebus out of it)), screenies have always appeared in my Photos 🤷‍♂️
 
Has anyone updated their watch to the newest watchOS 11.3 released today, 01/27? If so, is there any change to the screenshot automatic transfer problem?
 
I must admit I never knew this was a thing that you could take a screenshot from the AW.
I don't use it often. It was helpful in getting a developer to see an issue with layout and he corrected it.
 
I must admit I never knew this was a thing that you could take a screenshot from the AW.

My GF and I have a thing about math, and 10:01, 10:10, 11:11, 12:12, etc. have become secret code for "we are in synch!" ;)

1111.jpeg


I've bashed the beJebus out of my AW6 over the years . . . the crown works 93-44/100 of the time, but the side-button doesn't press-down/release like it once did.

The two, together, frustrate me to no-end these days . . . the thrill wears-off when a simple function ceases to be simple.
 
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