In 1996 the Connecticut Supreme Court ruled in Sheff v. O'Neill that the state must act against racial imbalance in its schools, no matter what the cause. The ruling in Sheff v. O'Neill concerned Hartford 's public schools, which had a 95 percent minority population, while schools in adjacent suburbs were over 90 percent white. Basing its ruling on the provision of the Connecticut Constitution barring segregation, the court held that students in the Hartford public schools were racially, ethnically and economically isolated, and that, as a result, Hartford public school students had not been provided a substantially equal educational opportunity as guaranteed by the state constitution. 

Milo Sheff was a fourth grader when the suit was first filed in 1989 on his behalf and that of 16 other students.  The Connecticut Supreme Court ruling was not the end of their legal battle.  Instead, the state and city dragged their feet when it came to implementing the ruling and fighting segregation and inequality in schools.  The Harford schools remained 95 percent Black and Latino.  In 2000 the plaintiffs went back to court and asked the state to dramatically expand magnet schools, which were designed to draw students from the suburbs into Hartford .  In 2003 the plaintiffs and the Governor reached a temporary settlement to establish eight new magnet schools, but in 2004, 15 years after the case was originally filed, Black parents were back in court, demanding more resolute action on the part of Hartford and state officials.  Milo Sheff, whose name is attached to a suit that has been considered a kind of Brown v. Board of Education for Northern schools, is now a prominent hip-hop artist in Connecticut .  

In 2008 the US Court of Appeals for the Second Circuit ruled that a public high school in Burlington did not violate a student’s First Amendment rights when it removed her as class secretary and prevented her from again running for office after she posted a vulgar and misleading message about a rock concert at Lewis Mills High School on the blog she created on her home computer. The court did not accept the argument that the 16-year-old student could not be punished because her offense occurred off campus and was unlikely to disturb the running of the school. Instead it ruled that her blog posting was intended to “come onto the campus” and her misleading report that the conference had been cancelled after being postponed three times could have caused a significant disruption. The court argued that forms of electronic communication such as blog postings, instant messaging and emails make it difficult to limit the authority of the school to the physical campus and that the offensive language she used was potentially disruptive and could have been banned if used in school.

(The US Court of Appeals for the Second Circuit has jurisdiction over New York and Vermont as well as Connecticut).

During the 1983 school year, some students in Waterbury School District wore baggy clothing to school in violation of school policy.  They were suspended. The school argued that the baggy clothing could be to conceal weapons. The students went to court and challenged the constitutionality of the dress code.  The Superior Court of Connecticut upheld the dress code, accepting the school district's argument that it was necessary to maintain a safe school environment for students.