The ‘Two-Dismissal Rule’ – 11^th Circuit (Florida Law)

Great Lakes Insurance SE v Bryan Crabtree
No. 23-12020, 2026 WL 1392075 (11th Cir. May 19, 2026)

The U.S. Court of Appeals for the Eleventh Circuit affirmed summary judgment for policyholders Bryan and Bethea Crabtree (the Crabtrees), holding that Great Lakes Insurance SE’s (Great Lakes) second voluntary dismissal of its declaratory judgment action operated as a dismissal with prejudice under Federal Rule of Civil Procedure 41(a)(1)(B), barring Great Lakes from pursuing a third lawsuit on the same claim.

The Crabtrees purchased an insurance policy from Great Lakes covering their boat, which suffered extensive fire damage while stored in Florida. When the Crabtrees demanded payment, Great Lakes denied coverage and filed a declaratory judgment action in the District of Montana. The parties then agreed that Great Lakes would voluntarily dismiss the Montana suit without prejudice and refile in the U.S. District Court for the Southern District of Florida (SDFL), with the Crabtrees agreeing not to contest service, venue or personal jurisdiction. Great Lakes dismissed the Montana case and immediately commenced a second declaratory judgment action in the SDFL.

The Crabtrees responded by filing a counterclaim against Great Lakes in Florida state court and moving to stay or dismiss the SDFL federal lawsuit pending resolution of the state court claims. Great Lakes contended the Crabtrees’ actions breached their agreement, but rather than respond to the Crabtrees’ motion, Great Lakes voluntarily dismissed its Florida federal action and filed a third declaratory judgment suit back in the District of Montana. The Crabtrees moved to dismiss under Rule 41(a)(1)(B): the “two-dismissal rule.” The parties later consented to transfer the case back to the SDFL, where the district court granted summary judgment to the Crabtrees.

Rule 41(a)(1)(B) provides that “if the plaintiff [has] 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.” Great Lakes argued that the two-dismissal rule should not apply because the first dismissal was by mutual agreement with the Crabtrees. Great Lakes maintained that the rule’s purpose, preventing “unreasonable use of the plaintiff’s unilateral right to dismiss,” was not served when one dismissal was consensual.

The appellate court rejected this argument, writing that “Rule 41(a)(1) means precisely what it says” and courts may not “elevate general notions of purpose over the plain meaning of the text.” Under Supreme Court precedent, an “adjudication on the merits” within the meaning of Rule 41 is simply “an acceptable form of shorthand” for a dismissal with prejudice. Once a claim is dismissed, the plaintiff is barred from any later lawsuit on the same claim, regardless of whether a prior dismissal was by agreement.

Great Lakes also argued that the bar should not apply because it had refiled in Montana and then agreed to transfer to, rather than directly refiling in, the SDFL. The appellate court again disagreed, noting that whether the third suit was originally filed in the SDFL or transferred there, Great Lakes was seeking to prosecute a later lawsuit on the same claim, which it could not do. The appellate court affirmed summary judgment in the Crabtrees’ favor, concluding that Great Lakes’ second voluntary dismissal operated as a dismissal with prejudice, and any future action on that claim was permanently barred.

By: Chelsea Kormos