Third District Court of Appeal
State of Florida
Opinion filed August 12, 2026.
Not final until disposition of timely filed motion for rehearing.
No. 3D25-0630
Lower Tribunal No. 22-CA-840-K
Citizens Property Insurance Corporation,
Appellant,
vs.
Tracey Oppenheimer, et al.,
Appellees.
An Appeal from the Circuit Court for Monroe County, Timothy J. Koenig, Judge.
De Novo, and Kathryn L. Ender, for appellant.
Shochet Law Group, and Doreen Inkeles (Trenton), for appellees.
Before FERNANDEZ, MILLER and LOBREE, JJ.
FERNANDEZ, J.
Citizens Property Insurance Corporation (“Citizens”) appeals the trial
court’s “Order On Citizens Property Insurance Corporation’s Motion for
Sanctions Pursuant to Section 57.105, Florida Statutes,” which denied
Citizens’s motion. For the following reasons, we affirm.
FACTS AND PROCEDURAL HISTORY
The First Action – Case No. 3D22-0995
In 2016, Citizens issued a homeowners insurance policy to Tracey
Oppenheimer and Dr. Darren Oppenheimer (collectively, “plaintiffs”) for the
period December 9, 2016 to December 9, 2017. After plaintiffs reported
Hurricane Irma damages on September 21, 2017, Citizens investigated,
accepted coverage, and paid $28,914.12. Plaintiffs demanded appraisal,
after which Citizens issued supplemental payments totaling more than
$212,000.00.
In March 2019, plaintiffs sued Citizens in the Sixteenth Judicial Circuit
in and for Monroe County, Florida (case number 19-CA-000274-K) (the “first
action”) for breach of contract, seeking additional coverage for the reported
loss. In December 2021 and January 2022, Citizens served multiple
proposals for settlement, including proposals of $250 to each plaintiff (or
$500 jointly) dated December 10, 2021, and a joint proposal for $100,000
dated January 28, 2022. On December 29, 2021, Citizens’s counsel advised
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plaintiffs’ counsel via email that the $240/$500 proposals were a mistake and
made an informal global offer of $85,000. Citizens later asserted it was too
late to serve enforceable amended proposals because trial was less than 45
days away.1
On January 6, 2022, Dr. Oppenheimer filed a notice accepting the
December 10, 2021 proposal and later filed a voluntary dismissal with
prejudice based on a written settlement agreement. On February 3, 2022,
Tracey Oppenheimer filed a notice accepting the January 28, 2022 joint
proposal as to her individually and filed a voluntary dismissal with prejudice,
later amending it to remove a reference to a February 3, 2022 proposal for
settlement.
Thereafter, Citizens moved to strike Dr. Oppenheimer’s acceptance of
the December 10, 2021 proposal, contending that the $250 figure resulted
from a clerical error and that it had intended to serve each plaintiff with an
inclusive proposal for settlement for $42,500. Citizens alleged that Dr.
Oppenheimer’s acceptance should be stricken because there was no
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Citizens contends that throughout the proceedings, plaintiffs attached proposals for settlement and associated releases which appear to be for $42,500.00 to each plaintiff. Citizens alleges this is misleading because the only reason plaintiffs have copies of the unserved proposals for settlement for $42,500 is because their counsel asked to see them, as Citizens never served them on plaintiffs.
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pending proposal for settlement of $42,500. Citizens claimed it never
amended its notice and offered a global settlement offer pursuant to Danis
Indus. Corp. v. Ground Improvement Techs., Inc. 645 So. 2d 420 (Fla. 1994),
prior to this improper acceptance on the part of Dr. Oppenheimer. Citizens
further contended the only proposal for settlement that was pending on
January 6, 2022, was for $250 to each insured, which had been served on
December 10, 2021.
Plaintiffs filed their “Motion to Enforce Settlement and for Sanctions”
against Citizens. The motion addressed plaintiffs’ acceptance of two
proposals for settlement, one dated December 10, 2021, and another dated
January 28, 2022. The motion also acknowledged plaintiffs’ notices of
voluntary dismissal with prejudice.
Citizens responded, summarizing its informal offer for $85,000 to
resolve the litigation and explaining the mistake Citizens made when it
served the proposals for settlement. Citizens also acknowledged that it
“never filed an amended Notice of Serving Proposals for Settlement stating
the originally intended amounts.” The response argued that there was never
any meeting of the minds between the parties regarding the plaintiffs’
purported acceptance of the settlement offers and that Dr. Oppenheimer’s
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acceptance should be stricken in favor of acceptance of Citizens’ global offer,
which was at most $100,000.
After a hearing before the trial court, on May 11, 2022, the court denied
plaintiffs’ motion to enforce. The court found there was never a meeting of
the minds regarding the final settlement amount. Plaintiffs appealed, and on
December 6, 2023, this Court issued its per curiam affirmance in
Oppenheimer v. Citizens Property Insurance Corporation, 387 So. 3d 1210
(Fla. 3d DCA 2023).
The Second Action – 3D25-0630 (the appeal currently before this
Court)
While the first action was pending at the trial level, plaintiffs filed a
second action on December 27, 2022 (case no. 2022-CA-840-K) in Monroe
County, Florida (the “second action”). In this action, plaintiffs alleged two
counts for breach of contract relating to enforcement of the alleged
settlement agreements and two counts for equitable relief. The complaint
cited the first action and attached the proposals for settlement and plaintiffs’
notices of voluntary dismissal from the first action. Plaintiffs further attached
the unserved proposal for settlement to Dr. Oppenheimer in the amount of
$42,500. The complaint sought $142,500 in damages plus prejudgment
interests, costs, and attorney’s fees.
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Citizens moved to dismiss the complaint on multiple grounds, including
lack of jurisdiction, res judicata/collateral estoppel, statute of limitations,
sovereign immunity, and failure to state a cause of action. In the alternative,
Citizens requested the litigation be stayed pending resolution of the first
action.
Before Citizens’s motion to dismiss was heard by the trial court,
plaintiffs amended their pleading on February 3, 2023. Plaintiffs asserted the
same two causes of action against Citizens based on the reported losses
and proposals for settlement; however, they dropped the equitable claims.
Citizens again moved to dismiss and later amended its motion to include this
Court’s per curiam affirmance issued in the first action.
Without leave of court, in March 2024, plaintiffs then filed a second
amended complaint. Plaintiffs replaced their breach of contract claims with
two unjust enrichment claims, while still seeking the same damages based
on their alleged acceptance of the proposals for settlement.
On July 26, 2024, Citizens moved to dismiss the second amended
complaint, raising the same reasons for dismissal as before. Citizens also
argued that the second amended complaint was a nullity as it was not filed
with leave of court.
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On July 26, 2024, Citizens served plaintiffs and their counsel with a
section 57.105 safe-harbor notice and proposed sanctions motion. Citizens
argued that plaintiffs and their counsel knew or should have known that their
actions were in bad faith and were unsupported by fact or law. After plaintiffs
did not withdraw or correct the second amended complaint within the 21 days
required by section 57.105(4), Citizens filed its sanctions motion with the trial
court on August 20, 2024.
The trial court ordered plaintiffs to respond. Instead, plaintiffs withdrew
their second amended complaint as improperly filed and requested leave to
file a third amended complaint. Thereafter, the trial court denied Citizens’s
motion to dismiss as moot. The trial court further ordered that Citizens’s
motion for sanctions be rescheduled so that it could be heard along with
plaintiffs’ motion to amend. The hearing date was set for January 30, 2025.
Plaintiffs’ motion for leave to amend asserted the same claims set out in the
second amended complaint. Citizens filed a response in opposition.
On January 8, 2025, Citizens served plaintiffs and their counsel with a
second safe-harbor notice and proposed motion for sanctions. The January
8, 2025 safe harbor letter demanded dismissal of plaintiffs’ lawsuit. Plaintiffs
voluntarily dismissed their lawsuit without prejudice on January 24, 2025,
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which was day 16 of the 21-day safe harbor period. Thus, Citizens never
filed their January 8, 2025 sanctions motions with the trial court.
On January 30, 2025, the trial court held the hearing on Citizens’s
motion for sanctions. Citizens argued that the hearing was directed at the
motion for sanctions it had filed on August 20, 2024. Plaintiffs’ counsel
argued that Citizens’s January 8, 2025 safe harbor letter and the motion
raising the same reasons as its August 20, 2024 motion gave plaintiffs
another chance to avoid sanctions.
Citizens argued that their motion for sanctions was the one directed to
plaintiffs’ second amended complaint. Citizens explained that the motion for
sanctions was based on 1) plaintiffs filing the second amended complaint
improperly without leave of court; 2) Citizens’s immunity from litigation
because the allegations fall outside of a claim under the insurance policy;
and 3) res judicata and collateral estoppel because the issues in this litigation
had already been decided in the first action. Citizens also contended that
plaintiffs did not file their Notice of Withdrawal until after the safe harbor
period expired. Thus, Citizens argued that plaintiffs’ demand for $142,500
from the settlements was unsupported by fact or law and was purely
frivolous, warranting sanctions against plaintiffs and their counsel.
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Plaintiffs’ counsel argued that Citizens could not move forward on its
August 20, 2024 motion for sanctions because it served plaintiffs with a
different safe harbor letter and proposed motion after the August 20, 2024
motion for sanctions was filed. The trial court asked whether Citizens could
demand sanctions based on a prior motion made under section 57.105.
Citizens argued that it was allowed to do so even though plaintiffs had
subsequently filed a voluntary dismissal without prejudice. The trial court
noted that the January 8, safe harbor letter contained the same points,
arguments, and request for relief Citizens raised in its earlier August 20, 2024
motion. The trial court restated its concern that when multiple motions for
sanctions are served based on the same points, “the last one you get is your
final opportunity.” The court further stated:
THE COURT: Here's why. Here's why, I would say. First of all,
the case that he cited, and your Safe Harbor letter ties into the
case that he cited in this regard. And let me, it says, "As
explained in the enclosed motion for sanctions, and as further
addressed in Citizens' opposition to plaintiffs' motion for leave to
amend the first amended complaint filed on January 2025, and
in Citizens' prior motions to dismiss filed on March 12th and July
26th" – here it is -- "we firmly believe that your pursuit of this
litigation is not in good faith, and is unsupported by any facts or
then existing law." And you go through and you talk about
everything that you've talked about in your argument here….So
it suggests in its own language that you continue to pursue this,
and we're giving you another chance to not do that.
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Citizens’ counsel responded to the court, “I agree with you, that’s exactly
what it did.” Counsel then explained that Citizens served the January 8 letter
and motion so that it would be entitled to fees up through the January 30
hearing on entitlement. Plaintiffs’ counsel countered that if entitlement to
sanctions were found, Citizens would have been entitled to fees all the way
up to through the hearing on entitlement without having to serve the extra
motion on January 8. Plaintiffs’ counsel argued that because Citizens did
serve the extra motion and safe harbor letter, it gave plaintiffs the opportunity
to withdraw their claim again and avoid sanctions.
The trial court denied Citizens’s motion for sanctions, relying on case
law presented by plaintiffs, including Lago v. Kame By Design, LLC, 120 So.
3d 73, 75 (Fla. 4th DCA 2013), and Phillips v. Garcia, 147 So. 3d 569 (Fla.
3d DCA 2014). The trial court concluded that where successive safe-harbor
notices are served on the same grounds, the last notice controls. Thus, it
found plaintiffs’ voluntary dismissal within that 21-day safe harbor period
allowed them to avoid sanctions. Thereafter, on March 15, 2025, the trial
court entered its order denying Citizens’s motion for sanctions for the
reasons stated on the record at the January 30, 2025 hearing.
ANALYSIS
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On appeal, Citizens argues that the trial court’s order denying its
motion for sanctions must be reversed and remanded because there is no
Florida precedent invalidating a motion for sanctions under section 57.105
when the moving party serves a subsequent motion directed to further
frivolous pleadings and motions. Plaintiffs respond that the trial court
correctly denied Citizens’s August 20, 2024 section 57.105 motion because
their successive January 2025 motion afforded the plaintiffs a final
opportunity to avoid the possibility of sanctions being imposed.
A trial court’s order denying a motion pursuant to section 57.105 is
reviewed under an abuse of discretion standard. AT&T Mobility, LLC v.
Rigney, 388 So. 3d 72, 81 (Fla. 3d DCA 2023). However, when the trial
court’s denial is based on an issue of law, the appellate court reviews the
order under a de novo standard of review. Id. Section 57.105, Florida
Statutes (2025), provides:
(1) Upon the court’s initiative or motion of any party, the court
shall award a reasonable attorney’s fee, including prejudgment
interest, to be paid to the prevailing party in equal amounts by
the losing party and the losing party’s attorney on any claim or
defense at any time during a civil proceeding or action in which
the court finds that the losing party or the losing party’s attorney
knew or should have known that a claim or defense when initially
presented to the court or at any time before trial:
(a) Was not supported by the material facts necessary to
establish the claim or defense; or
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(b) Would not be supported by the application of then-existing
law to those material facts.
***
(4) A motion by a party seeking sanctions under this section must
be served but may not be filed with or presented to the court
unless, within 21 days after service of the motion, the
challenged paper, claim, defense, contention, allegation, or
denial is not withdrawn or appropriately corrected.
(Emphasis added).
This appeal presents an issue of first impression: whether a plaintiff’s
timely voluntary dismissal in response to a later-served, successive section
57.105 sanctions motion – raising the same grounds as an earlier motion
already filed – precludes sanctions on the earlier motion. On this record, the
trial court correctly denied Citizen’s August 20, 2024 motion because
Citizens later served a January 8, 2025 sanctions motion on the same
grounds, thereby affording plaintiffs a new 21-day safe harbor period and a
final opportunity to avoid sanctions, which plaintiffs did by dismissing their
action on day 16.
Plaintiffs ground their position on the two cases they presented to the
trial court, Lago and Phillips. We agree that these cases support the safe
harbor framework of section 57.105.
First, in Lago, the appellees’ initial motion for section 57.105 fees
contended that appellants’ fee motion was frivolous because there was no
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contractual or statutory basis for appellants to recover an attorney’s fees
award. Lago, 120 So. 3d at 74. That motion was served with the required 21-day safe harbor letter. Id. Appellee’s second motion for 57.105 fees included
the same arguments as the first motion, but also raised an additional
argument, that appellants had waived any right to recover attorney’s fees in
failing to request fees in a pleading. Id. The trial court entered an order
granting appellee’s second 57.105 motion and imposing sanctions against
appellants. Id.
The Fourth District Court of Appeal found that because appellee’s
second motion did not comply with the 21-day safe harbor provision set out
in the statute, the trial court erred in granting that motion. Id. Accordingly, the
appellate court reversed and held that when a subsequent or amended
section 57.105 motion raises a new argument, it must independently comply
with the 21-day safe harbor requirement. Id. at 75. In the case before us,
there was no independent ground raised by Citizens in its motion, plaintiffs
dismissed their case on day 16 of the 21-day safe harbor period.
Next, in Phillips, plaintiff Garcia filed a lawsuit against Phillips claiming
damages for false arrest and malicious prosecution. Phillips, 147 So. 3d at
570. In March 2007, Phillips served Garcia with a safe harbor letter/request
for dismissal pursuant to section 57.105(4). Id. Phillips argued that the
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lawsuit was frivolous because there was no material evidence to support the
malicious prosecution claim. Id. This letter/request was filed with the court
on February 5, 2009. Id. Thus, it was filed after the 21-day safe harbor period
expired.
Before filing her section 57.105 motion with the court, Phillips moved
for summary judgment in June 2008, contending that there was no evidence
for any elements of the malicious prosecution claim and that she was entitled
to qualified immunity. Id. at 571. On January 12, 2009, the trial court granted
Phillips's motion for summary judgment, ruling that she was entitled to
qualified immunity from Garcia's lawsuit. Id.
On January 6, 2012, Garcia and her counsel filed a motion for section
57.105 sanctions, which had been served on Phillips and her counsel in
August 2011, because the basis for granting summary judgment for Philips
was qualified immunity and not because there was no proof of the malicious
prosecution elements. Id. After a hearing, the trial court denied both section
57.105 motions.
Both parties appealed, and this Court affirmed and held that 57.105
sanctions are not automatic merely because a party ultimately prevails. The
movant must establish the claim was meritless under section 57.105. Thus,
Phillips is consistent with Lago.
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Here, Citizens served two safe-harbor motions asserting the same
bases as to why the plaintiffs’ amended complaints were frivolous (including
sovereign immunity, failure to state a claim, law of the case, res
judicata/collateral estoppel, and statute of limitations). Citizens
acknowledged the January 8 service was intended to preserve additional
fees through the entitlement hearing. However, by serving the successive
motion, Citizens effectively provided plaintiffs another safe harbor
opportunity. Plaintiffs took that opportunity and avoided sanctions by
dismissing their complaint within the 21-day safe harbor period. Accordingly,
on this record, the trial court did not err in denying Citizens’s 57.105 motion
for sanctions filed on August 20, 2024. We thus affirm the trial court’s order
denying Citizens’s motion for 57.105 fees
Affirmed.
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