Back when Win95 just showed up and allowed you to give your files longer names AND had some system files with longer names I did something stupid like that. I was doing something DOS based, attempted to do something or other to an entire directory and DOS shortened everything to 8 characters. That is, the first 6 original letters of the file name + ~1. So, for example, WIN95BOOOTFILE.BAT would have turned into WIN95B~1.BAT (or ~2 etc if that created a duplicate).
That, was a mess. Luckily, I’d been using DOS based operations for long enough that I managed to rename most of them by hand, just from memory, the rest, IIRC, I could figure out when the system called for the file, couldn’t find it and asked for it. Then all I had to do is go to the folder where it was looking for the missing file and rename the file it had truncated to what it wanted it to be called.
That seemed like an oversight on MS’s part. After giving Windows the ability to have file names that could be longer than 8 characters, they should have given DOS the ability to deal with them as well. I can’t be the only person that had that happen.