Topic: Gem reinstallation and errors after updating Debian 6


I'm relatively new with rails and I have some ruby apps installed on the server at work.

What I've been noticing is that every time that we do a update of the OS  (Debian 6) we have to reinstall some gems or reconfigure the apache conf for the vhosts that run ruby.

When we install a new ruby app the others are most likely going to break once done resulting in having to reconfigure the.

I've been reading and searching different sources to find similar situations but no luck so I was wondering what I'm doing wrong coz I don't really think that it's supposed to react that way.

Any help on the subject would be much appreciated.