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Are these files that are within LR or are they actual files in the finder itself
That appears to be a LR issue. Somehow it’s protecting them.
Try holding the option key or the command key down as you attempt to trash them. Also, in the get info box, check privileges at the bottom. Another way is select file and then hold down the command and option key at the same time and hit delete key
Lightroom does not store the image files. Instead, the LR catalog is a database that points to your image files. The Lightroom Queen (https://www.lightroomqueen.com/) is one website that can give you more information, if you want. However, you can use the Mac OS Finder to look at your external SSD. Pick out a file name you wanted to delete and see if you can do so (move it to the trash) in Finder. If not, get a friend who knows Macs to come over and help you out. This does not sound like a LR issue.
I have had that problem recently. I discovered that if I go to my external hard drive and manually delete a file from there and then empty trash, the delete function works in Lightroom Classic again. I hope this help someone, as it took me a lot of trying various things to find a solution.
Barry - cannot tell you how grateful I am for your guidance. Have been using LR for years, and this problem pops up occasionally. My normal fix was to copy my backup drive, clean the drive, and then reload the data. This is so easy - nuts, but it works!
