A mediated settlement agreement must be enforceable for its obligations to be binding. Several elements can result in mediated settlements being set aside: the absence of contractual certainty to bind the disputing parties, rescission on account of an unjust factor, undue influence, duress and coercion, unconscionability, incompetence or incapacity, lack of authority, fraud and mistake. The jurisprudence resulting from attempts to evade mediated settlement agreements provides guidance to the mediator and the legal advisors to the parties on the practical steps that can be taken to provide certainty and avoid enforcement problems. Careful and comprehensive drafting incorporating all the intended commercial terms is critical to ensure that mediated settlement agreements are complete and enforceable. Where compliance may be an issue, the settlement can be converted into an arbitral award or a court judgment, or enforced under the Singapore Convention which elevates international mediated settlement agreements to a new status that can be recognised and enforced within the framework of private international law.