Diligence and Timeliness under Rule 60(b)(6) for Settlement Enforcement: Sheppard v. Big Horn County

Introduction

In Sheppard Trucking v. Board of County Commissioners (2025 WY 31), the Wyoming Supreme Court confronted the question whether a litigant may invoke Wyoming Rule of Civil Procedure 60(b)(6) to undo a dismissal with prejudice entered under Rule 41(b)(1) for failure to prosecute—where the parties had an executory, un-reduced-to-writing settlement. Harold Sheppard, Jr., who operated a vintage‐plane salvage and trucking business at the South Big Horn County Airport, sued the county commissioners to block enforcement of a large storage lien. After extensive pretrial activity, the case stalled when the parties reached an oral settlement at a September 2022 status conference but never reduced their agreement to a signed document. Fifteen months later, the county moved to dismiss for lack of prosecution; the district court granted dismissal with prejudice. More than two months after that ruling, Sheppard sought relief under Rule 60(b)(6), arguing “unusual circumstances” justified enforcing the settlement before dismissal. The district court denied relief, and the Supreme Court of Wyoming, exercising abuse‐of‐discretion review, affirmed.

Summary of the Judgment

The Supreme Court’s unanimous opinion, authored by District Judge Eames, addressed two core questions: (1) whether the district court abused its discretion in denying relief under Rule 60(b)(6), and (2) whether Sheppard’s motion was filed within a “reasonable time.” The Court held that Sheppard failed to demonstrate the “unusual circumstances” required for extraordinary relief, that he had not diligently protected his interests by finalizing or enforcing the settlement, and that he waited too long—over two months after dismissal—to invoke Rule 60. Accordingly, the Court affirmed the denial of Sheppard’s motion and left intact the dismissal with prejudice for failure to prosecute, clarifying that Rule 60(b)(6) may not be used as a backdoor appeal or a shield against the natural consequences of a party’s own delays.

Analysis

Precedents Cited

Webb v. State ex rel. Dep’t of Fam. Servs. (2020 WY 111) – Articulates the abuse‐of‐discretion standard for reviewing Rule 60(b)(6) motions, and reaffirms that courts may refuse relief when a party has made “free, calculated, and deliberate choices.”
Myers v. Myers (2022 WY 75) – Stresses that Rule 60(b)(6) relief is reserved for “unusual circumstances” and cannot redress a party’s own failure to act.
Essex Holding, LLC v. Basic Properties, Inc. (2018 WY 111) – Holds that Rule 60(b) is not a substitute for a direct appeal of an adverse judgment.
MSC v. MCG (2019 WY 59) – Explains the Rule’s purpose “to relieve a party from the oppression of a final judgment … on a proper showing where such judgments are unfairly or mistakenly entered.”
Winney v. Jerup (2023 WY 113) and Meiners v. Fulkerson (2019 WY 26) – Provide guidance on what constitutes a “reasonable time” for filing a Rule 60(b)(6) motion.
Kennedy v. Kennedy (1971) – Historical precedent on the extraordinary nature of relief under the predecessor to Rule 60(b)(6).

Legal Reasoning

The Court divided its analysis into two main lines of inquiry:

Existence of “Unusual Circumstances.” Under Rule 60(b)(6), a movant must show “any other reason that justifies relief,” but only truly extraordinary situations will satisfy that threshold. The Court observed that Sheppard and his counsel had 15 months—and several procedural vehicles—to perfect their settlement or to seek judicial intervention, yet they did not. Instead of filing a stipulation of dismissal, moving to enforce the settlement, or even requesting a status conference, Sheppard let the case lie fallow. By “free, calculated, and deliberate” choice, Sheppard bore the risk that the county would seek dismissal, and the district court reasonably concluded that these were not the “unusual circumstances” warranting equitable relief.
Timeliness—“Reasonable Time.” Rule 60(c)(1) requires that any Rule 60(b) motion be filed “within a reasonable time.” While Wyoming appellate decisions have declined to fix rigid deadlines, they instruct courts to weigh finality, reasons for delay, the movant’s ability to discover grounds for relief, and prejudice to other parties. Here, Sheppard waited over two months from the date of dismissal—and weeks from delivery of the county’s opposition—to propose relief. His counsel conceded it “took a while” to prepare the motion and that other matters were prioritized. The Supreme Court held that under the particular facts, this delay was too long and reinforced the district court’s denial.

Impact

This decision clarifies several points for Wyoming practitioners and courts:

Rule 60(b)(6) remains an extraordinary remedy, not an after-the-fact lifeline for parties who miss deadlines or fail to reduce settlements to writing.
Litigants who negotiate oral settlements must promptly memorialize them (e.g., by filing a Rule 58 order or a stipulation), or risk subsequent dismissal for inactivity.
Parties seeking relief from a final judgment must move quickly once they identify grounds for relief—significant delays, even of a few months, may render a motion untimely.
District courts have broad discretion to weigh diligence, prejudice, and finality in deciding Rule 60(b)(6) motions; appellate review will defer to those judgments absent manifest unreasonableness.

Complex Concepts Simplified

Rule 41(b)(1) Dismissal With Prejudice: A court may dismiss a plaintiff’s case “with prejudice” if the plaintiff fails to prosecute or comply with court rules or orders. “With prejudice” means the case is over and cannot be refiled.
Rule 60(b)(6) “Any Other Reason”: This catch-all provision allows a court to relieve a party from a final order for reasons other than those specifically enumerated. The bar is high: the movant must show truly exceptional circumstances, not mere regret or tactical error.
“Reasonable Time” Requirement: Unlike certain Rule 60 grounds that prescribe firm deadlines (e.g., one year for newly discovered evidence), Rule 60(b)(6) simply requires action within a reasonable period. Courts look at factors such as how long the party waited, what steps they took, why they delayed, and whether the delay harmed the other side.
Executory Settlement Agreement: An agreement is “executory” when all material terms have been agreed upon but the formal documents have not yet been signed or the agreed consideration (payment, lease, transfer of property) has not been completed.
Abuse of Discretion Standard: Appellate courts will uphold a district court’s discretionary ruling unless it exceeds the bounds of reason—i.e., no reasonable judge could have reached the same conclusion under the circumstances.

Conclusion

Sheppard Trucking v. Board of County Commissioners reaffirms that Rule 60(b)(6) is an extraordinary remedy reserved for truly exceptional cases. Parties who reach an oral settlement must act promptly to reduce it to a binding order or document. Failure to do so, and to pursue relief without undue delay, risks dismissal with prejudice for failure to prosecute. The Wyoming Supreme Court’s decision underscores the duty of litigants to protect their own interests, the importance of timely post-judgment motions, and the broad deference accorded to district courts in managing their dockets and applying equitable principles.