I generally set up servers with "important" services listening on nonstandard ports (e.g. SSH != 22) and rename or completely remove root/admin users. I recently thought that it might be fun to create an external jailed root (and happily decorated) account to keep an eye on the kiddies.**
Of course, breaking in must seem stupidly easy... but not too easy. Is there anyway to allow multiple passwords to let a user login to an account? I'm think about using a few from common dictionaries for Hydra/John the Ripper, and of course "password1" and "superman" will be on the list.
If Linux user management (Debian specifically) isn't accommodating enough for faux fun of this sort, what scripts exist that could emulate an SSH/SFTP login experience and dumping the guest into a deliciously sticky honeypot?
**Addition: I would never put a honeypot on a production server; however, if I were to forward them to another server through a firewall, the question remains the same: is it possible to allow multiple passwords for a user?