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I use an external file system. It is safer. Sometimes, Windows decides it isn't going to remount the external file system right away. So when Photoshop comes up, it finds that the recent file I want to open cannot be found. After manually remounting the file system, it is there, but Photoshop has cleverly decided to remove that entry from the recently opened list. Except that doing that is not particularly clever. I'd report this on Adobe's bug reporting system, but Get Satisfaction is not satisfactory in their login behavior. I've registered, I can successfully go through their login process, but the submission page will not recognize my being logged in. I've reported this issue to Get Satisfaction, but they told me directly that Adobe pays their bills (implying that they do not care). Someone with an actual contact with a real Adobe person ought to run this up the line. That cannot be me because I have no official way to contact Adobe.
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My recent files list works exactly as expected. Photoshop CC 20.0.4 release on Windows 10.
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So it doesn't sound like anything is wrong with Photoshop here. It's operating as expected, and the issues is "Windows decides it isn't going to remount the external file system right away". When you first launch your computer does it make sense to open an explorer window and make sure your drive is mounted before booting up PS?
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I guess I was not quite clear enough. Yes, indeed, it is correct for PS to say it cannot find the file. Once I have reconnected the file system, however, it would be pretty nice to still have the recent entry still in the list. Instead, *AFTER* reconnection, that entry is no longer in the list because it could not find it earlier. I am sure it is "as designed", but the design is not as helpful as it could be.
P.S. For many good, historical reasons, I do *NOT* trust Windows to be free of intrusions. So, I keep my files on a file server and carefully allow write access only to those files that I will be working with. It would be nice to convince Windows to mount foreign file systems at boot time, but Microsoft knows what I want better than me, so I need to double check the mounts at boot. Sometimes, I forget. I do not like Windows.