1. First day on the job, email to boss: "Hey, the computer lab at Springfield High has a ton of known security flaws that are begging to be exploited."
2. Reply, 1 week later: "Sorry, we don't have any money for that. Just keep everything up-and-running."
3. 3 weeks later the computer lab at Springfield High got "hacked". All the computers displayed a popup window that said, "Miss Krabappel is a dyke!" (sorry for the offensive language)
4. Next day, email from boss: "The computer lab at Springfield High was hacked! Figure out how to fix this and make sure it doesn't happen again!"
5. A few days later Miss Krabappel filed to sue the school district. The local newspaper picked up the story.
6. Email from boss, in full panic mode: "I need you to figure out who hacked the computer lab at Springfield High so we can report him to the police!"
7. A week later an independent consulting firm was brought in to help identify the person behind the "hack". I heard they were paid $50K and found nothing. However, the kid got ratted out when he told all his friends. (It wasn't Bart Simpson! ;) )
8. Several weeks later: meeting to discuss working with a consulting firm that's gonna fix all the security issues because the current staff (me and my team) lacks the skills.
9. About 6 months later, I quit.
I worked for them as a contractor for a while and one of the big issues they had was they had tons of money to implement new technology (mostly from grants and things like that), but nearly nothing to maintain old tech. They could buy new computers all day long, but if something needed to be repaired/updated/maintained, there was no budget or resources to do it. So there were all sorts of fun issues, like they would buy computers and before they could get deployed their warranty would expire (since they weren't allowed to buy 3 year warranties on the computers) and computers with bad HDDs would get disposed of, even though the fix might be $50 and 10 minutes of time.