We were asked to make available over the web certain applications which were not designed for use in a "hostile environment", yet required access to a sensitive database. Also, it had to be possible for relatively inexperienced programmers to put those applications on the web. To do so without appreciably dimishing the security of the database, or that of the web server (Apache in a chroot), we poked a tiny hole through the wall of the "chroot prison" to implement a highly controlled channel of communication between CGI programs in the chroot, and fragile applications running on the system. Hole-in-the-chroot version 1 has been operational since mid-1999.