If you carry Florida auto insurance, or you did any time since 2023, an insurer probably owes you money right now. Dairyland’s dividends started going out this week. The catch is that some of it arrives as a paper refund, and a paper refund goes to the last address the company has for you.
Go update that address. Especially with the carrier you left.
Dairyland, owned by Sentry, said on August 31 it is returning $30 million to eligible Florida private passenger auto policyholders as a one-time dividend. If you owe a balance, it comes off the balance and future bills. If you are paid in full, or your policy was canceled with nothing due, you get a refund. Eligible policyholders should start seeing theirs within 14 to 21 days.
It is not just them. USAA announced a $500 million dividend in June for roughly 830,000 Florida members who held auto policies between 2023 and 2025. Progressive is crediting close to $1 billion to about 2.7 million Florida personal auto policyholders, announced back in October 2025. In 2025, Florida’s top five auto insurers, 78 percent of the market, cut rates an average of 6.5 percent.
Where the money came from
Florida’s 2022 and 2023 legal changes barred assignment-of-benefits agreements and one-way attorney fees. Litigation and defense costs fell. An actuarial report by Dave Moore of Moore Actuarial Consulting and James Lynch, the former chief actuary at the Insurance Information Institute, commissioned by the American Property Casualty Insurance Association and reported September 3, found Florida policyholders paid almost $3 billion less in premiums in 2025 than the year before. Auto rates fell 4.1 percent. Homeowners rates rose less than 1 percent after years of double-digit jumps.
A.M. Best’s line on it: “Instead of being a poster child for abusive claims, Florida has become a role model for legislative regulatory relief.”
Take the win. Then watch the wording, because this is where drivers lose money.
A dividend is not a rate cut
They are two different pockets, and you want both.
Dairyland did both: a one-time $30 million dividend and, separately, an average 14 percent cut to its Florida auto rates. Those are unrelated events. The dividend is a refund of past profit. The rate cut only reaches you when your renewal gets written on the new filing.
Run the numbers on a $2,400 policy. A one-time dividend of a couple hundred dollars is nice and it happens once. A 4 percent rate decrease is about $96, and it repeats every year you stay. The recurring one is worth more. Most drivers only notice the check.
Do this week
Log into every Florida auto carrier you have used since 2023, including ones you left, and confirm the mailing address on file. Two minutes each.
Open your current bill and look for a credit line. Progressive’s money moves as a credit on active policies, not a check, so it is easy to miss.
Call your agent and ask one question: is my current premium written on the most recent approved rate filing? If the answer is no, ask what the number looks like on the new one.
Then shop it anyway. Carriers are cutting at different speeds, which is exactly when the gap between your carrier and the next one gets wide. Our insurance estimator gives you a baseline, and the how to lower your premium guide covers the levers worth pulling before you switch. GEICO customers, note that its Florida cuts were filed without disclosed amounts or dates. Ask.
One caveat
Dividends are not promises. Insurers declare them out of good years, and Florida just had a stretch of them. Nothing obligates any carrier to repeat this in 2027. Collect what is on the table now, get your renewal repriced, and budget as if the next one is not coming.
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Sources
- Floridians Saved Almost $3B on HO and Auto Premiums Last Year, Actuarial Report Finds (Insurance Journal, September 3, 2026)
- Sentry's Dairyland to Return $30 Million to Florida Auto Insureds (Insurance Journal, August 31, 2026)
- Progressive to refund nearly $1 billion to Florida auto insurance policyholders, Gov. DeSantis says (CBS Miami)