At work, when we split off and became our own company, I suggested we use google for our domain to handle our email. We're tiny and don't have an IT department.
Nope. My boss wanted an open source app called Zimbra. He put one of the tech support guys in charge of learning it and installing and maintaining it.
It was a nightmare from day one. Took him days to install and my officemate and I both had to get involved and help get things going. Once it was going, it was never totally configured right. The support guys would make changes they didn't understand and then swear to me that no changes were made when I was called in to help get it working again.
We got it up and relatively stable, but it went down again two days ago. Database issues. Got it up again. This morning it was down. We were hacked.

I spent the morning cleaning up that mess.
Guess whose company is moving to google mail in a day or two?
