I had brought an Knoppix disc to class one day and booted up to it, just to show the other kids in the class how you can go about removing a password off of a Windows box. When my teacher saw this, he became furious, but he not because of what I was doing per se. He had no idea what Knoppix was (he kept referring to it as Windows 95) and he wasn't happy that I was teaching the other kids something that wasn't on the curriculum. This was before class started, it wasn't on his time, but for some reason, it really pissed him off. At the time I didn't know what to make of it.
The previous year, I was doing some research in the library at school for a paper I was supposed to be writing. I had brought a flash drive with some documents on it to save stuff to. When I had plugged it in and gone to My Computer, I noticed that _tons_ of teachers had shared drives publicly available with a lot of sensitive stuff (IE gradebooks) on them. Now, most students wouldn't know how to get to some of the stuff, but I didn't think that mattered. After I finished doing my research, I went to the IT lady at school, told her what I had found and showed her exactly how to get to the stuff. She got on to me for "hacking into the school system" and told me to go back to class because they had it covered.
The point I am trying to make is that the school districts really need to get a handle on technology, the people maintaining it, and the teachers teaching it. There are too many educators/sysadmins just barely getting by with things that they learned 5, 10, or even 20 years ago, and it is affecting the entire system, whether they realise it or not.
I do understand that schools have a limited supply of educators. I guess it just goes back to the whole "Those who can, do. Those who can't, teach.".