I have recently been having problems with running Typo on Textdrive. The cause seems to be that the ruby grows too big and is killed by FreeBSD. Why it isn’t being restarted automatically by lighttpd, I don’t know. The solution is supposed to be to start the rails fastcgi program separately from the lighttpd process. I just finished switching my lighttpd config to the new recommendation in the [Textdrive knowledge base](http://help.textdrive.com/index.php?pg=kb.chapter&id=71).
One thing which seems interesting for the future is [mongrel](http://mongrel.rubyforge.org/), a Ruby web server. It sounds like it could be proxied to and replace lighttpd.