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Sometimes (not all the time), I try to delete photos from my library in the Lr Desktop application, but weeks later they will reappear. I've now wasted hours deleting large batches of photos, which I then have to re-delete one or two more times.
One reason suggested was that this was a memory-card sync issue. If you delete photos from your libary, and then import photos again from your camera's memory card, even if you select "don't import duplicates," you will re-import past photos beacuse Lightroom won't detect deleted photos as duplicates. I don't think this is the issue I'm encountering, though. I'm pretty disciplined with wiping my memory card.
I suspect the reason has to do with a glitch in the sync between my desktop Lr library and my Adobe Cloud Lr library. Maybe I delete photos on my desktop app and when it finally syncs up online (sometimes weeks later since I work in low-internet areas), the photos get added back into my desktop Lr library from the cloud backup.
Whatever the cause, this is a huge headache for me since I'm going back to re-delete hundreds and hundreds of photos. Deleting photos should be a simple operation in 2023, especially for a software package as expensive as Adobe. Plus they're charging me for the storage than I'm unable to delete photos from. Such a pain. Thinking of switching to Luminar.
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Do it online, lightroom.adobe.com. That is the "master". I always delete from there and then permanently delete.
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Unfortunately, since I have inconsistent and slow access to internet, using lightroom.adobe.com doesn't work for me. I just need the desktop app to work.
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That is your answer. If your internet connection isn't working, the files aren't being deleted online and won't be deleted. Lightroom is online - the images live in the cloud. The desktop app is just a conduit.
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iPhoto works the same way - photos are stored in the cloud - but I can reliably delete photos on my iPhone and laptop. Apple has never messed up my deleted photos in the 10+ years I've been using their (free) software.