This is a good one:

I have a user that has made a file called "hhhhhhhhhhhhhhiiiiiiiiiiiiiieeeeeeeeee.....doc"
but a lot longer. This file is now invulnerable. I can't delete it, I can't rename it, I can't open it. Context menu is....short. Open, Edit, New, Print, Open With and Send to are the only options I get the rest aren't even there, not greyed out, just gone.

Last time I had this problem it was with folders, someone made
h:\new folder\new folder\new folder\new folder\new folder\new folder\new folder\new folder ..... and it was too long to handle, but that said "folder is too long to delete" so I moved some of it to a higher directory then deleted it.

This fails silently and just won't do anything. Won't move, won't delete, won't rename.

Any suggestions?