Mac OS Catalina vs. 10.15.7 with LrC updated to current version. When I delete a photo, LR asks if I want to delete from lightroom or the disk. Previously, choosing delete from the disk always sent the photo to trash. Since the latest update, those files don't show up in trash unless I shut down the computer and reboot it and then I am able to see then in the trash can. Files from other programs show up in trash normally when I delete them. Is this a bug with the latest update and is there a fix?
Are your images on an Internal or external drive? If external is that drive Active, Not Asleep (as OS X likes to put external drives to sleep ASAP), when you Delete from disk.
On reboot of the system it wakes all external drives and at that time your images are recorded as being in the trash. They are never Moved to the Trash can. Just a Reference is made that they have been placed in the trash and if the drive they are on is not Active that can't happen.
Do a test. With LrC open use Finder to Browse the drive the pictures are on to make sure it is awake and active before you try the Delete from disk option and do they then show up in the trash without a reboot?