Case Law Update: Breakwater Commons v. Empire Indemnity — Insured Wins Trial Fees, Loses Appellate Fees

Updated September 28, 2026. A Southwest Florida condominium association that spent more than six years fighting its insurer just learned that winning the case is not the same as being paid for every stage of it. On September 16, 2026, the U.S. District Court for the Middle District of Florida, Fort Myers Division, ruled in The Breakwater Commons Association, Inc. v. Empire Indemnity Insurance Company, No. 2:20-cv-31-KCD-KRH, that Breakwater is entitled to its attorney's fees as the prevailing party at the trial level — but denied the portion of its request covering an earlier trip to the Eleventh Circuit, because no fee application was ever filed in that court.

What happened

Breakwater Commons Association sued Empire Indemnity Insurance Company over payment under a commercial property policy; the case landed in federal court in January 2020 on a notice of removal, docketed as a breach-of-contract insurance action. Along the way the parties fought over Breakwater's right to an appraisal. Empire took an interlocutory appeal from the appraisal ruling, and the Eleventh Circuit dismissed that appeal for lack of jurisdiction.

Back in the district court, Breakwater prevailed on its breach-of-contract claim and obtained confirmation of the appraisal award. The court entered final judgment for Breakwater on June 30, 2026. Breakwater then moved for fees and costs under Florida's insurance fee-shifting statutes, sections 627.428 and 626.9373, Florida Statutes. Empire did not contest that Breakwater was the prevailing party, and agreed Breakwater was entitled to reasonable fees incurred at the trial court level.

The ruling: a circuit rule you cannot skip

The only real dispute was the appellate work. Eleventh Circuit Rule 39-2(a) says that, absent an exception, an application for attorney's fees "must be filed with the clerk within 14 days" after the time to seek rehearing runs. Breakwater never filed one after Empire's interlocutory appeal was dismissed.

The court agreed with Breakwater on one point: Rule 39-2 is not jurisdictional. As the order put it, "[o]nly Congress may determine a lower federal court's subject-matter jurisdiction," citing Kontrick v. Ryan, 540 U.S. 443, 452 (2004). But the court held that "removing the jurisdictional label does not make Rule 39-2 optional," relying on Gray ex rel. Alexander v. Bostic, 613 F.3d 1035, 1043 (11th Cir. 2010): a party who wants fees for appellate work must file a timely petition with the circuit clerk.

Breakwater's two escape routes both failed. It argued that because the Florida fee statutes condition a fee award on "the rendition of a judgment," the state statute supplied the timing and displaced Rule 39-2. The court disagreed, reasoning that the Florida statutes "dictate the substance of a fee claim, establishing when and how an insured's right to collect fees ripens," while "the Eleventh Circuit decides how and when the bill must be submitted." It also declined to read Rule 39-2(e) — which lets a party skip the circuit application when a reversal produces a remand — to cover this situation, because Empire's appeal was dismissed rather than reversed. See Common Cause/Georgia v. Billups, 554 F.3d 1340, 1357 (11th Cir. 2009).

The court acknowledged the practical unfairness Breakwater raised: in 2023, when the appeal ended, no judgment yet existed, so there was no ripened statutory right to fees. Its answer was that Rule 39-2(d) already accounts for that. That subsection lets any party who "is or may be eligible" for appellate fees file a motion to transfer consideration of those fees to the district court — in effect, a placeholder filed while the merits are still unresolved.

The motion was granted in part and denied in part. The court also directed Breakwater to hold the supplemental fee motion required by Local Rule 7.1 until 14 days after Empire's pending appeal is decided, provided Breakwater remains the prevailing party. That appeal has not been decided, and this order is not the last word in the case.

What this means if you have a Florida property claim

Three practical points, none of them a prediction about any particular case:

• Fee rights can be won on the merits and lost on the calendar. Breakwater was the undisputed prevailing party and still did not recover its appellate fees. If your case takes a detour to an appellate court — even a detour the insurer started and lost — the deadline for claiming fees for that detour runs in that court, on that court's rules.
• A placeholder costs little. The court pointed to Rule 39-2(d) as the mechanism Breakwater had available. Where appellate fee eligibility is uncertain because the merits are unresolved, discussing a protective filing with appellate counsel within the 14-day window is worth raising early.
• Check which fee statutes apply to your policy. Breakwater's claim arose under a policy predating Florida's recent fee-shifting overhaul. Verified against the Legislature's official site on September 28, 2026: sections 627.428 and 626.9373 appear in the 2022 Florida Statutes but do not appear in the 2026 Florida Statutes. Chapter 2022-271, Laws of Florida (Senate Bill 2-A), had already amended section 627.428(1) to provide that in suits arising under a residential or commercial property insurance policy, fees "shall be awarded only as provided in s. 57.105 or s. 627.70152, as applicable." Sections 57.105, 627.70152 and 86.121 remain in the 2026 Florida Statutes. Which framework governs your claim depends on your policy's date, so confirm it rather than assuming.

Appraisal-driven condominium and commercial property cases like this one are common in Southwest Florida, and the fee question is often worth more than the parties expect by the time a case reaches judgment. For background on the underlying claim process, see our guides on filing a Florida hurricane damage claim and working with a property damage attorney in Fort Myers. More rulings are collected on our Case Law & Industry Insights page.

If your Florida property insurance claim has been denied, underpaid, or delayed, Louis Law Group offers a free case evaluation. Nothing in this article is legal advice, and no outcome in any case is predicted by it. Facts described above are taken from the court's September 16, 2026 order and the public docket in Case No. 2:20-cv-31-KCD-KRH (M.D. Fla.).