Rule 41(a)(1)(B) Two-Dismissal Rule Applies Even When the First Dismissal Is by Agreement; Second Notice Dismissal Is With Prejudice and Bars Relitigation in the Same Court (Including After Transfer)

Case: Great Lakes Insurance SE v. Bryan Crabtree
Court: Court of Appeals for the Eleventh Circuit
Date: 2026-05-19
Panel: Newsom, Lagoa, Kidd, Circuit Judges (Opinion by Newsom, J.)

1. Introduction

This appeal arises from an insurer’s effort to avoid coverage for a boat fire through a federal declaratory-judgment action. Great Lakes Insurance SE (“Great Lakes”) denied Bryan and Bethea Crabtree’s claim, asserting noncompliance with policy conditions. The litigation’s central significance is procedural: Great Lakes filed and then twice voluntarily dismissed substantially identical federal actions—first in the District of Montana, then in the Southern District of Florida (“SDFL”)—before filing a third time in Montana, which was later transferred back to SDFL.

The key issue on appeal was whether Federal Rule of Civil Procedure 41(a)(1)(B)’s “two-dismissal rule” rendered Great Lakes’s second voluntary dismissal an “adjudication on the merits,” thereby operating as a dismissal with prejudice and barring the third action once it arrived in SDFL.

2. Summary of the Opinion

The Eleventh Circuit affirmed summary judgment for the Crabtrees. It held that:

  • Rule 41(a)(1)(B) “means precisely what it says,” and its text controls over purpose-based arguments.
  • A second voluntary dismissal “operates as an adjudication on the merits,” which the Supreme Court has equated with a dismissal with prejudice.
  • Once Great Lakes’s claim was dismissed with prejudice, it could not be litigated again in SDFL—even though the third case was originally filed in Montana and only later transferred to SDFL (with Great Lakes’s consent).

3. Analysis

3.1. Precedents Cited

Standard of review and interpretive posture

  • Amerisure Ins. Co. v. Auchter Co., 94 F.4th 1307 (11th Cir. 2024) — Cited for de novo review of summary judgment. This framed the appellate posture: no deference to the district court’s legal conclusions about Rule 41’s effect.
  • Hemispherx Biopharma, Inc. v. Johannesburg Consol. Invs., 553 F.3d 1351 (11th Cir. 2008) — Cited for de novo review of interpretations of the Federal Rules of Civil Procedure.

Textual primacy in interpreting Rule 41

  • Est. of West v. Smith, 9 F.4th 1361 (11th Cir. 2021) — Quoted for the proposition that “Rule 41(a)(1) means precisely what it says.” This served as an Eleventh Circuit anchor for a plain-language approach.
  • ASX Inv. Corp. v. Newton, 183 F.3d 1265 (11th Cir. 1999) — Cited for the method: “look to the plain language of the rule and read it as a whole.”
  • Villarreal v. R.J. Reynolds Tobacco Co., 839 F.3d 958 (11th Cir. 2016) (en banc) — Used to reject “elevat[ing] general notions of purpose over the plain meaning of the text.” This directly rebutted Great Lakes’s request to read a purposive exception into Rule 41(a)(1)(B).

The disputed purposive “exception” and why the court rejected it

  • Poloron Products, Inc. v. Lybrand Ross Bros. & Montgomery, 534 F.2d 1012 (2d Cir. 1976) — Great Lakes’s principal authority for the idea that the two-dismissal rule should not apply when one dismissal was by stipulation/party agreement, because the “fear of unilateral abuse” diminishes. The Eleventh Circuit acknowledged the argument but declined to follow it, emphasizing it “needn’t get into” res judicata’s purposes because Supreme Court authority and Rule 41’s text resolve the issue.

Supreme Court decisions providing controlling meaning of “adjudication on the merits”

  • Cooter & Gell v. Hartmarx Corp., 496 U.S. 384 (1990) — Treated as decisive: the Supreme Court described the second Rule 41(a)(1) dismissal of the same claim as one that “must be dismissed with prejudice.” The Eleventh Circuit used this to translate Rule 41(a)(1)(B)’s phrase “adjudication on the merits” into its operative consequence: with prejudice.
  • Semtek Int'l Inc. v. Lockheed Martin Corp., 531 U.S. 497 (2001) — Critical in two ways:
    • It interprets “adjudication upon the merits” (Rule 41(b)) as an acceptable shorthand for “with prejudice.”
    • It relies on the contrast within Rule 41(a) between “dismissal without prejudice” and “adjudication upon the merits,” reinforcing the same equivalence for Rule 41(a)(1)(B).
    The Eleventh Circuit further invoked Semtek’s practical implication: once dismissed with prejudice, “the same claim” can’t be “refil[ed]” in the same court.

Secondary authority

  • Dismissal With Prejudice, Black's Law Dictionary (12th ed. 2024) and With Prejudice, id. — Used to reinforce the ordinary legal meaning: a with-prejudice dismissal “finally disposes” of the claim and “bars any future action on that claim.”

3.2. Legal Reasoning

(a) The court’s rule is textual and categorical

The court read Rule 41(a)(1)(B) as a two-step structure:

Default: “Unless the notice or stipulation states otherwise, the dismissal is without prejudice.”

Exception: “But if the plaintiff previously dismissed any federal- or state-court action based on or including the same claim, a notice of dismissal operates as an adjudication on the merits.”

From that structure—especially the contrast signaled by “But”—the court concluded that “adjudication on the merits” functions as the “opposite” of “without prejudice,” i.e., a dismissal with prejudice. That inference was not left to linguistic logic alone: Cooter & Gell v. Hartmarx Corp. and Semtek Int'l Inc. v. Lockheed Martin Corp. supplied authoritative confirmation.

(b) The court refused to create a “stipulated-dismissal” carve-out

Great Lakes urged the court to adopt Poloron Products, Inc. v. Lybrand Ross Bros. & Montgomery’s purposive limitation: because the first dismissal in Montana was pursuant to an agreement, the two-dismissal rule’s anti-gamesmanship rationale would not be served.

The Eleventh Circuit rejected that invitation on interpretive and hierarchical grounds:

  • Interpretive: under Est. of West v. Smith, ASX Inv. Corp. v. Newton, and Villarreal v. R.J. Reynolds Tobacco Co., the court must enforce Rule 41’s text as written.
  • Hierarchical: Supreme Court interpretations of “adjudication on the merits”/“upon the merits” in Cooter & Gell v. Hartmarx Corp. and Semtek Int'l Inc. v. Lockheed Martin Corp. foreclose a contrary, purpose-driven exception.

Notably, the panel emphasized the parties’ own concessions: they agreed that Rule 41 applied, that two actions based on the same claim were previously dismissed, and that the second dismissal “operate[d] as an adjudication on the merits.” The dispute was therefore narrowed to whether the court would nonetheless decline to apply the rule—an approach the court viewed as incompatible with textual interpretation and controlling precedent.

(c) The “filed elsewhere then transferred” argument fails

Great Lakes attempted to avoid Semtek’s same-claim-in-same-court bar by distinguishing between “refiling” in SDFL and having the case transferred there from Montana. The Eleventh Circuit rejected the distinction for two reasons:

  • Fact: Great Lakes consented to transfer, undercutting any effort to characterize SDFL’s involvement as purely involuntary.
  • Law: the bar is functional: once a claim is dismissed with prejudice, the plaintiff may not “prosecut[e] any later lawsuit on the same claim.” Whether the case arrives in the same court by filing or transfer does not change that it is a “later lawsuit” seeking “future action” on a claim already disposed of with prejudice.

3.3. Impact

Immediate doctrinal impact in the Eleventh Circuit

  • No “agreement” exception to the two-dismissal rule (at least where the second dismissal is a unilateral notice under Rule 41(a)(1)(A)(i)). Even if the first dismissal occurred pursuant to an agreement between the parties, the second voluntary notice dismissal still triggers Rule 41(a)(1)(B)’s “adjudication on the merits” consequence.
  • “Adjudication on the merits” under Rule 41(a)(1)(B) is treated as “with prejudice” in the strongest operational sense: it forecloses further litigation of the same claim in the same court.
  • Transfer does not sanitize a barred claim. A plaintiff cannot evade a with-prejudice effect by filing in another district and then transferring (or consenting to transfer) into the barred forum.

Practical impact for litigants (especially in coverage/declaratory actions)

  • Strategic caution on voluntary dismissals: Plaintiffs (including insurers) must treat a second Rule 41(a)(1) notice dismissal as potentially case-ending, not as a procedural reset button.
  • Forum maneuvering risks: Where a case bounces between jurisdictions (e.g., due to forum-selection clauses, service/venue agreements, or parallel state-court actions), parties must carefully track how many times an “action based on or including the same claim” has been voluntarily dismissed.
  • Reduced room for “purpose” arguments: The opinion signals that equitable narratives (reliance, perceived gamesmanship by the other side, fairness) are unlikely to defeat the two-dismissal rule’s text where Supreme Court precedent has supplied a clear meaning.

4. Complex Concepts Simplified

  • “Voluntary dismissal” (Rule 41(a)(1)(A)(i)): A plaintiff may dismiss a case on its own—without a judge’s order—by filing a notice before the defendant files an answer or a summary-judgment motion.
  • “Without prejudice” vs. “with prejudice”:
    • Without prejudice means the claim can generally be brought again later.
    • With prejudice means the claim is finally over and cannot be brought again.
  • “Two-dismissal rule” (Rule 41(a)(1)(B)): If a plaintiff has already dismissed one action based on the same claim, then dismissing the second action by notice converts that second dismissal into an “adjudication on the merits” (i.e., with prejudice).
  • “Adjudication on the merits” in Rule 41: Despite sounding like a judge decided who was right, it is a procedural label that—per Cooter & Gell v. Hartmarx Corp. and Semtek Int'l Inc. v. Lockheed Martin Corp.—functions as “with prejudice” for purposes of ending the claim.
  • “Claim preclusion / res judicata”: A doctrine preventing the same parties from relitigating the same claim after a final disposition. Great Lakes argued about res judicata’s “purpose,” but the Eleventh Circuit emphasized that Rule 41’s text and Supreme Court interpretations controlled the outcome without a purpose-driven exception.

5. Conclusion

The Eleventh Circuit’s decision in Great Lakes Insurance SE v. Bryan Crabtree reinforces a strict, text-centered application of Rule 41(a)(1)(B): a plaintiff’s second voluntary notice dismissal of the same claim is an “adjudication on the merits,” meaning a dismissal with prejudice, and it bars further litigation of that claim in the same court—even if the first dismissal was by agreement and even if the later action reaches the court by transfer rather than direct refiling.

In the broader procedural landscape, the opinion serves as a warning that voluntary-dismissal sequencing can be outcome-determinative: once the two-dismissal rule is triggered, case strategy yields to finality.