When I was in high school (not so long ago, but quite some time in computer years), we tested the limits of free speech with t-shirts, the occasional flyer, buttons, and even editorials in the school paper. Freedom of speech was largely an issue of students speaking freely while they were at school.
Now, however, since so much of what students do happens online for the whole world to see, the boundaries of free speech have become more complicated. As Lewis S. Mills High School senior, Avery Doninger, found, even calling someone a douchebag on your personal blog can apparently meets the criteria of "substantially disruptive to the educational environment" (the usual test for whether a student's speech is protected under the First Amendment). A post in Ars Technica describes how she was punished for the contents of her blog and how the punishment was upheld by the US Court of Appeals last week:
Avery then made a post on her personal blog while at home, outside of school hours. In it, she used somewhat unladylike language to describe school officials, and called on other students to write or call in their complaints...The blog post contained no threats and was fairly benign outside of her use of the word in question. Although the blog post is no longer online, it's excerpted in some of the court filings:
"jamfest [a battle of the bands that Avery and the student council were coordinating] is cancelled due to douchebags in central office...And here is a letter my mom sent to [school officials] to get an idea of what to write if you want to write something or call her to piss her off more."
This post became a problem when school administrators found it via an Internet search and then prevented Avery from running for class office as a result. As the article points out,
The decision concerns free speech advocates because of the cloudy nature of the blog post. No threats were made and no major student demonstrations occurred—at most, the students were a bit "riled up" (according to Avery's testimony) over having their event possibly cancelled and their student council going to great lengths to turn the decision around. Most importantly, the decision will likely be used as further precedent in the future for schools (and possibly colleges and universities) to take action against students for their postings around the 'Net.