I’ve had similar issues before with software glitches causing files to disappear, but I’ve always been able to recover them thanks to regular backups. I use Time Machine on my Mac to back up everything, so if you’ve been using Time Machine too, here’s how you can try to restore your missing PDF files:
Step 1: Click on the Time Machine icon in the menu bar or go to System Preferences > Time Machine.
Step 2: Go to the folder where your PDFs were stored. In your case, it could be in the Documents or Books folder.
Step 3: Use the timeline on the right side of the screen to scroll back to a date before your files went missing. Since you started trying to transfer them on February 17, you can look for backups from a few days before that.
Step 4: Once you find the missing PDFs, select them and click the Restore button. They should return to their original location.
If you don’t have a Time Machine backup, there are other file recovery tools that might help recover lost files, such as 4DDiG Mac Data Recovery, Disk Drill, Data Rescue, DMDE. Hopefully, one of these options will work for you!