In this article we report on qualitative research in which we probed the opinions and views of a purposive sample of high-profile and influential role players in education about aspects of education litigation in South Africa since 1994. This year marked the transition to a democratic government in South Africa, and resulted in a new education system, which has led to a great deal of litigation, as was to be expected. Our participants were personally involved in litigation in various capacities. Their responses to our questions reflected hope, but also concern, and even despair. In their opinions almost all of the disputes were between the state and its citizens, and that the state lost virtually all cases. State officials often ignored legal advice and acted on “imagined powers”, causing embarrassment to the state where they seemed insensitive to the needs of the people, and sometimes deliberately transgressed prescripts and provisions, abandoning its mandate to children and the country more broadly. There is extreme concern about the tendency of officials to ignore court orders. No lessons seem to have been learned from judgments and infractions of the same kind occur repeatedly - even if litigation seems to have consumed between 4–6% of the education budget. There was surprise that cases dealt almost exclusively with disputes about stake-holders‟ powers, and that few human rights and social issues have been litigated. Furthermore, individual officials that seemed to suffer no consequences from their unlawful actions and showed an apparent lack of professionalism to acquaint themselves with the legal prescripts that govern their professional work, caused concern for our respondents, as did the destructive role that unions and politicians seemed to play in education. However, litigation has nonetheless led to the clarification of some issues.