During one week when I was managing IT for a small rural school, I encountered two examples of how educators do not understand the nature of enterprise systems. On Monday, a teacher brought me a sale paper for a local box store retailer (it was early in the holiday gift buying season). She told me she had $300 left in her classroom budget, and she wanted to buy a laptop that was on sale for $250. On Tuesday, I was getting ready to install the replacement for the 48-port switch that had failed, causing the whole floor of the school to lose connection. A teacher asked what I was doing when she saw me carrying the switch into the closet where it was installed (literally a closet… this was an old school building). When I said, “this is the new switch,” she reacted with surprise and said, “I thought you were replacing something like a light switch.” Both teachers described here are individuals who could accurately be labeled “tech-savvy” because of their use of IT in their classrooms and their web presence.