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Over the past twenty-five years, the state of Florida has been recognized across the United States as a leader in the development of court-connected alternative dispute resolution programs. Mediation, in particular, has flourished across the state, with one hundred eleven programs in place in family, civil, community, and dependency sectors. Administrative support and oversight for court-connected mediation programs are provided by The Florida Dispute Resolution Center (DRC) - the administrative arm of the Florida Supreme Court - housed within the Office of the State Courts Administrator. In collaboration with the DRC, we designed and conducted a benchmarking study of seven selected mediation programs in the family, civil and community sectors. Our focus in this article is on certain insights that emerged at the macro level regarding the very nature of court-connected mediation, as we analyzed and tried to develop explanations for our empirical findings. Specifically, we will address the fundamental value-based dilemma of court-connected mediation programs, three different approaches to addressing this dilemma through which mediation programs and the courts have forged their relationship in Florida, and some implications of these insights for practice and policy.