Frontline Insurance vs Security First Insurance

Verdict

Both are privately held Florida property insurers without an AM Best rating, and in 2025 NAIC data Frontline ranked #29 among U.S. groups ($1.16 billion) and 9th in Florida (4.63% of premiums), while Security First ranked #65 ($333.3 million, roughly 1.8% of the Florida market). The gap is footprint and how you buy. Frontline writes in Alabama, Delaware, Florida, Georgia, Maryland, North Carolina, South Carolina, Tennessee and Virginia, only through independent agents. Security First writes only in Florida, through independent agents and direct by phone and online quote.

The policies are built around different ideas. Frontline's signature feature is the optional Stepdown Deductible, a separate policy that returns a growing share of your hurricane deductible: up to 5% in year one, rising to up to 100% after the fifth renewal, if you report the claim within 90 days and the loss at least equals the deductible. It also requires its own Home Checkup inspection, and an incomplete one can lead to cancellation or nonrenewal. Security First leads with Premier, an HO-5 for Coverage A of $500,000 to $5 million that pays belongings at replacement cost, and Signature+, an HO-3. Its homeowners forms can carry several deductibles (hurricane, all-other-perils, water and roof), though an optional Disappearing Deductible cuts some of them 20% for each claim-free year.

Roofs are where Security First is most specific. Its optional Roof Surfaces Payment Schedule endorsement pays wind and hail roof damage on a sliding scale, for a composite shingle roof up to 100% under one year old, 80% at five years and 60% at 10. Frontline's profile gives no roof settlement terms, so ask. New Florida Frontline homeowners policies are now issued by Frontline Insurance Reciprocal Exchange (since July 9, 2026), whose subscribers make surplus contributions of 10% of premium, according to KBRA.

Choose Frontline if

• You live outside Florida in one of the other eight states, or you own a coastal home in the Carolinas, Georgia or Virginia.
• You want Stepdown Deductible protection and will report any hurricane claim within 90 days.
• You need high-value coverage (Florida homes valued at $1 million and up), builders risk, or flood and excess flood from the same agent.
• You are comfortable completing a required Home Checkup and joining a reciprocal exchange in Florida.

Choose Security First if

• You own a Florida home worth about $500,000 or more and want an HO-5 with open-perils contents at replacement cost.
• You want to buy direct by phone or online quote, with service through the MySFI portal, app and live chat.
• You will trade coverage for price, through the roof payment schedule or limited water coverage (capped at $10,000), and you understand both are reductions.
• You value a published reinsurance program: $1.48 billion of total limit for 2026-2027, with $970 million available for a single event.

Key differences

Before you decide

Get quotes for the same Coverage A, hurricane deductible and endorsements, and ask each agent whether the carrier is binding at your address; Frontline restricts binding during hurricane watches and warnings. Compare roof terms and the water and roof deductibles. reciprocal exchanges: how they work covers the Frontline exchange, hurricane and named-storm deductibles explained helps price Stepdown against a higher deductible, Roof payment schedules and ACV roof endorsements explains Security First's roof schedule, and Financial strength ratings: AM Best, S&P, Moody's and Demotech shows how to compare a KBRA rating with a Demotech one.