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Hi, I've been having this bug where randomly all pop up windows stop appearing. For example after I do a save as and choose a location, the next dialog box with my compatibility settings doesn't appear. Photoshop acts as if it is visiable so I either have to press ESC or Return though I have no visible pop up box to adjust. Please help. Usually I get it to work again after restarting the computer but I've done that twice now and no luck. Using photoshop 22.4 on Mac Pro tower running Catalina 10.15.7
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Are you expecting that window that came up, asking if you wanted to make the file compatible (keep a flattened version within the file)? That's turned off as a preference, now. You can turn it back on at Photoshop>Preferences>File Handling and set Maximize PSD and PSB File Compatiblity to Ask, instead of Always.
 
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No, it's ALL pop up windows. That was just an example. I ended up uninstalling and reinstalling photoshop and that fixed the issue so far. Fingers crossed!
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Hi there, I'm running into this issue after upgrading to PS 22.5.3 also on Catalina 10.15.7 .... it's quite frustrating. I un- and reïnstalled the same version which seemingly fixed it... until yesterday when it started not showing any kind of pop-up window again. I quit PS 3 or 4 times, retry retry retry and open files and then do anything and sometimes, also completely random it seems, it just works like normal again. I love the PS dev team for introducing so many new features over the years but they came with an equal amount of new unwanted 'features' (yes, BUGs) as well....
If for some reason you can't upgrade to the latest osX and the PS of 2-3-4 versions ago Adobe 'service' pretty much leaves you hanging...
Like everyone should just have enough money to buy the latest Apple hardware.
Anyways, I'm done complaining.... what version of PS are you running currently?
(I didnt attach any screenshots of pop-up windows not showing up 😉
BR
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I'm getting the same with osx 12.5 on a Mac Studio, so I think its an Adobe thing, not that you need newer apple hardware (and to be honest, the mac studio has been a terrible experiance)