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If your files are large and your free space is small, the OS will deleted the oldest/largest files instead of storing them in the trash. Could this be what is happening? Start with an empty trash bin and then try to delete an image from inside LR.
Thank you for taking the time to reply but unfortunately that is not it. Taken so long for anyone to answer (two weeks), I've been in constant contact with Adobe technical services and seems like I have actually found a bug in the Lightroom software as they were able to replicate the problem when working with an external hard drive.
Hopefully won't be long before they have an update...
I have the same issue in LightRoom CC 2015.9. I mark for deletion .dng images in the Grid view of the Library by pressing X and then go to the Photo / Delete rejected photos menu options, making sure I also click the Delete from Disk button. I confirm that the file is deleted from it's directory on the external hard drive using Finder however it is not in the Trash.
Similar to James' report, having observed the Trash was definitely empty, I deleted an image DIRECTLY from within its directory using Finder and went to the Trash to see if it was there and it was - together with hundreds of other images that I had deleted from within LR over the last four hours.
I am using MacOS Sierra 10.12.4 on a Mac Pro and have 400GB of free space.
Its never happened before today for me.
Any ideas please?
I've just upgraded to LR 2105.10 however the issue has not been fixed. The missing "deleted by LR" images which should have been in the Trash can still be made to reappear in the Trash by deleting a photo using the Finder, so that's a good work-around.
The is some information here on a similar problem. Try performing the solutions discussed here.
I'm having the same problem. I delete files in bridge and lightroom... both show files deleted, however, they aren't in the trash. This poses a real problem as I'd like to recover files if I have accidentally deleted them. Has anyone found a fix to this???? By the way, I am a Mac user, and the problem hasn't always occurred.