get Google's Gmail for all students
Many students already forward their Microsoft webmail to Google Gmail accounts. Why not just give students Gmail that is connected with their @middlebury.edu email addresses.
It's called Google Applications. Google provides email to the school and it is tied to our middlebury.edu addresses. You use the same Gmail interface but with all of Google's goodies -- ease of use, HTML, conversation view, tags, etc.
Here's how it works: http://www.google.com/a/help/intl/en/edu/index.html