Phillip McCallum
MEDIATOR AND ARBITRATOR

In the world of civil litigation, achieving a settlement is often celebrated as the finish line. But for many parties, that moment is just the beginning of another chapter: ensuring the terms of settlement are honored and enforced . Without thoughtful structuring and enforcement mechanisms in place, even the most carefully negotiated agreements can unravel—leading to renewed conflict, additional costs, and frustration for all involved. This post explores several advanced settlement enforcement strategies that neutrals and attorneys should consider to promote long-term compliance and reduce the risk of post-resolution disputes.  1. Built-In Performance Milestones & Timelines Including clear, time-bound performance obligations within a settlement agreement (e.g., staggered payments, deliverables, corrective actions) gives parties a roadmap for success—and provides the court or a neutral with enforceable benchmarks should compliance issues arise. 🔹 Example: “Party A shall remit $25,000 in three installments due on the 1st of each month, beginning [Date]. Any missed payment beyond 5 business days will trigger stipulated penalties.” 2. Liquidated Damages & Stipulated Penalties Agreed-upon financial consequences for non-compliance can be powerful deterrents. When drafted carefully, liquidated damages clauses or stipulated penalties can simplify enforcement by preemptively setting terms for breaches—especially in cases where proving actual damages would be complex or expensive. ⚠️ Caution: These provisions must be reasonable and not punitive to be enforceable under most state laws. 3. Incorporating Arbitration or Binding Mediation for Enforcement For settlements that anticipate ongoing interaction or the possibility of interpretive disputes, consider designating a neutral to oversee or arbitrate future enforcement issues . This allows for faster resolution of compliance challenges without returning to the court system. 🔐 Tip: Add an “enforcement neutral” clause—appointing a mediator or arbitrator from the outset who is already familiar with the case history. 4. Confession of Judgment or Consent Judgment Clauses In appropriate jurisdictions, parties may agree to a confession of judgment or consent judgment , allowing for immediate court enforcement if the breaching party defaults. These mechanisms serve as a strong compliance incentive and bypass the need for a new lawsuit. ⚖️ Note: This must be handled carefully and ethically, ensuring all parties are represented and fully understand the implications. 5. Court Retention of Jurisdiction Ensure the court retains jurisdiction over the settlement agreement by incorporating appropriate language into the dismissal order. This provides a direct enforcement pathway through the same court—without the need to file a new action. 🧾 Sample Language: “The Court retains jurisdiction to enforce the terms of the parties’ settlement agreement as incorporated herein.” The best settlements don’t just resolve disputes—they prevent new ones from forming. At Schreiber ADR and in my practice we work closely with attorneys and parties not only to reach agreement, but to structure resolutions that last. Whether through strategic clauses, post-settlement check-ins, or retained enforcement jurisdiction, taking a proactive approach to settlement enforcement protects everyone’s investment in resolution.