I just got good news regarding a SF City recommendation… the people in the Workforce Investment Board are not liable regarding recommendations regarding Windows software, and we have a lot of insurance also. That's according to the lawyers at the private industry council of SF.
The deal is that we approved the use of Windows and SQL server, the standard Microsoft database solution, to hold sensitive citizen data. That's not, in my opinion, secure enough to satisfy a "due diligence" requirement for security. It required extensive firewalling, and duplicate networks to bring it up to acceptable levels of security.
Using Linux, life would be easier and cheaper, but sometimes you gotta work with what you got.
update: just to remind people, at craigslist we use Linux on server and increasingly on the client side, with much greater reliability and security, lower price.