What is the error message and does it affect all files you’re deleting or just one of a group?
This is the error message. It happens for any file in any catalog. I've used a couple of different external HD's over the years, and this still keeps happening. Seems to be an issue for people storing catalogs on external HD's. It's really maddening. You would think this issue would be fixed by now.
Like I said earlier, sometimes it magically correctly itself. Could take days. Sometimes weeks. I will say though that every time I restart my computer LR gives me this error message and I have to deal with this
Same thing here!
So you can delete the file, you just can't delete it and put it in the Trash. Sounds like your OS needs to do something to that external drive to permit proper operation of Trash. I'm not a Mac user, but here is a thread that may be helpful: Maverick. Can not empty trash from file from an... | Apple Support Communities. (I googled osx+mavericks+external+drive+trash to find this as the first hit. There are others.)
This issue was highlighted in another thread. My contribution to that one is repeated below...
I came across a workaround on the web in a forum (can't remember which one) and it's simple.
In the Finder, go to the root level of the external HD which contains your photos; create a new folder, call it anything. Immediately delete the folder.
Return to LR and you should find that photos delete normally after that.
This seems to reset the permissions problem though you have to repeat this workaround every time you reboot your Mac.
Hope this helps.
This is how I solved it, thanks to combined information posted on forums:
1. Got a new external hard drive formatted for Mac (I was using read-only Windows from my PC)
2. Created a folder in new external drive -imported to LR- send to trash- empty trash
3. The above was still not working until I noticed one day magically the missing picture icon started to show up in LR
4. I went to the "set as rejected"pictures- locate missing pic (and nearby ones)
5. Selected the pics -photo- remove- delete from disk
Thanks to the hours spent on searching different threads, and to the relentless users because LR never provided any kind of support or formal response to solve this by just letting users to getting lost in frustration .