Ok, I like to transfer and sync files between my machines via 100MB Zip disks because I currently do not have a home network setup. I realised awile ago that the linux ext2 file system was totally butchering long file names, so as making backups of my /home directory impossible without compression into a tar.gz file (which i dont want to do).

... so i started using the msdos vfat file system by mounting -t vfat and this seemed to preserve the file names just fine, but after swapping disks back and forth a few times it looks like the file names got butchered again!

Does anyone have an idea of what exactly causes this scrambling of file names? Could I have accidently mounted the disk incorrectly at some point?

thanks

Just to get the whole story straight:
Are you placing them in a .tar.gz file before you put them on the zip disk?
What filesystem are they originally on?
What filesystem are you using on the zip disk?
What filesystem are they ending up on?
What is the original long filename?
What is the resulting short filename?
How many bits are you using for FAT (12, 16, 32)?