The idea of a file to check works well..
But...

Where I work, noone logs onto servers as anything but administrator of a domain or of a machine. ALL other work is done on workstations (especially browsing the internet, word processing apps, email, etc.) Using this policy keeps our servers free from excessive junk files and security problems (see Microsoft's frequent security bulletins).

A simple rule: Unless the task is a direct operation on server functions, it probably shouldn't be done at a server console.

Brian