No problem. It put a smile on my face.
The problem as such isn’t that Windows has problems copying them back and forth, it is that the backup software and VSS can’t track the files and secure them (and a lot of the files were contracts, legal documents etc.), which would be a major problem if the files “disappeared”.
Stopping the user making too longer filenames is more important than being able to copy them. I had to manually go through and rename over 300 files and folders that were too long, so that they can be backed up.