Five by Five Aviation Insurance, the Zero-Claims First Year, and the Piston Market Opening Up

Five by Five Aviation Insurance, a Minneapolis-based carrier that launched in late 2025, completed its first full year of operations with zero claims against its policies. The company has now announced an expansion from turboprops and jets into newer piston aircraft, opening a new option for pilots flying modern glass-panel singles. This matters because it adds competition to a market that spent the better part of the last decade contracting.

What Is Five by Five Aviation Insurance?

“Five by five” is radio terminology for a signal that is loud and clear in both strength and quality - maximum strength, maximum clarity. Headquartered in Minneapolis, Minnesota, the company chose that name deliberately.

Five by Five entered the market focused exclusively on turboprops and jets. That is a common starting point for a new aviation insurer. Turboprop and jet operators tend to be higher-hour pilots flying under structured recurrent training regimens, making the underwriting profile more predictable. After completing year one with a clean loss record, the company announced it is extending its book of business to include newer piston aircraft.

How Five by Five Achieved a Zero-Claims First Year

Five by Five credits two factors: training requirements and data.

Traditional aviation underwriting relies heavily on self-reported information - total hours, ratings, a five-year accident and violation history. That model functions, but it doesn’t always capture how a specific pilot actually performs in a specific aircraft type.

Five by Five’s approach targets a more precise risk profile: not just total hours, but relevant hours in type; not just a rating on a certificate, but demonstrated currency and recency. When did the pilot last fly this category of aircraft? When did they last complete recurrent training? What specific scenarios have they trained for?

Requiring training as a condition of coverage - rather than simply offering a pricing credit for it - is a qualitatively different commitment. An insurer that mandates training is actively producing lower-risk pilots, not just selecting for them after the fact. Training becomes part of the product, not a box to check.

Which Piston Aircraft Are Now Eligible?

Five by Five’s expansion targets newer piston aircraft - a specific segment, not the piston fleet broadly. Aircraft that fall within scope include:

Cirrus SR series (SR20, SR22, SR22T)
Diamond DA40
Newer Cessna 172 and 182 with glass-panel avionics
Piper Archer with modern avionics
Columbia 350 and 400

The qualifier matters. Newer aircraft - generally those manufactured within the last 15 to 20 years with current avionics - represent a fundamentally different risk profile than older airframes with basic instrumentation. A Cirrus SR22 equipped with the Cirrus Airframe Parachute System (CAPS) was designed from the ground up with accident survivability as a core requirement. A Diamond DA40 was engineered with a crashworthy structure informed by decades of accident data. A newer Cessna 172 with an integrated glass panel gives pilots situational awareness tools that didn’t exist in general aviation cockpits 30 years ago.

Pilots flying older airframes - a 1968 Bonanza or a 1972 Cherokee, for example - should note that this specific expansion likely does not apply to their situation, though the broader market trend it represents is still relevant.

Why the GA Insurance Market Needed New Entrants

The general aviation insurance market entered a difficult period around 2017 and ran hard through 2020. Underwriters exited. Capacity shrank. Premiums rose - in some cases dramatically. Loss ratios had gotten out of hand, reinsurance markets tightened globally, and declining total hours flown in the GA pilot population made exposure modeling harder.

The pandemic briefly interrupted that pattern. Flying dropped in 2020, claims dropped with it, and some operators saw temporary premium relief. When activity recovered, claim activity recovered with it. The structural problems didn’t go away.

What genuinely improved the picture for certain fleet segments was better data paired with structured training requirements. The clearest example is the Cirrus fleet.

Cirrus worked directly with the insurance industry to establish recognized training standards for SR series pilots. The Cirrus Standardized Instructor Pilot (CSIP) program became a credentialed benchmark. Underwriters began offering meaningful credits to pilots who trained through that program, and the accident rate in the fleet reflected the investment. That correlation is not coincidental - it is what happens when training is made structural rather than optional and when clean loss data validates the connection.

Other manufacturers and type organizations followed similar paths. Diamond has factory training programs. The American Bonanza Society (ABS), Cessna Pilots Association, and Piper Owners Society all run structured programs that underwriters recognize. AOPA’s Air Safety Institute has built carrier relationships around its course catalog. Five by Five is entering a market where that framework already exists - applying a philosophy that has shown results in specific segments and extending it to a new book of business.

What Pilots Should Ask Before Buying a Policy

The specifics of a training requirement matter more than the existence of one. A requirement satisfied by any biennial flight review with any instructor is fundamentally different from one that specifies type-appropriate training with a defined curriculum and recognized instructors.

Before binding coverage with any insurer, ask your broker:

Is training a coverage requirement, or a credit that adjusts pricing?
What specific training qualifies - which programs, which instructor credentials?
Does the requirement address the aircraft type and category you actually fly?

Per AOPA reporting from September 2026, Five by Five is taking its data-driven and training-specific approach seriously. But as with any insurance product, read the actual policy language. “Recommended” and “required” are not the same word.

Coverage Basics Worth Revisiting

The Five by Five announcement is the news peg, but a few insurance fundamentals are worth reviewing for any GA pilot.

Agreed value vs. actual cash value. Agreed value means you and the insurer establish the aircraft’s worth up front - that figure is what you receive in a total loss, no depreciation argument. Actual cash value means the insurer determines market value at the time of loss, which can differ significantly from your expectation, especially in a used aircraft market that has been moving. Most aviation insurance professionals recommend agreed value for aircraft owners.

Non-owned aircraft coverage. If you regularly fly club aircraft, rental aircraft, or occasionally borrow another pilot’s airplane, your personal aviation policy may or may not extend to those operations. Non-owned coverage is often available as an add-on and is typically inexpensive relative to what it protects. Check your policy or ask your broker directly.

Dual instruction in your own aircraft. If you plan recurrent training or an instrument proficiency check with an instructor in the right seat, confirm your policy covers dual instruction. It almost always does - confirm it anyway.

Why This Matters for Pilots: The Bigger Picture

Five by Five’s zero-claims first year is a result worth noting, but it is one data point. What the company does in year two and year three - and as its piston book grows - will tell the real story.

The larger signal is the philosophy behind the result. Training-linked underwriting backed by granular, type-specific data is the direction the aviation insurance market is moving. When an insurer rewards training with coverage access and better pricing, and that correlation is validated against actual claims data, the cycle reinforces itself: more training produces better operations, fewer claims, and sustainable pricing that draws more pilots back toward training.

General aviation’s safety record has improved substantially over the past 30 years. Aircraft technology contributed. Avionics contributed. The analytical work of the FAA, AOPA, and the NTSB - pulling accident data apart to identify actual causation - contributed. But deliberate, structured, type-appropriate training is in that mix. The insurance market is one of the most powerful incentive structures available to push more pilots toward more of it.

For pilots shopping coverage for a newer piston aircraft, Five by Five is worth adding to the broker conversation as of September 2026. Not as a definitive recommendation - your situation is specific to your aircraft, your history, and your operation - but as a name to put on the table.

Key Takeaways

Five by Five Aviation Insurance (Minneapolis, MN) completed its first full year with zero claims, then announced expansion into newer piston aircraft.
The company attributes its loss record to training requirements as a condition of coverage and data-driven underwriting that goes beyond total hours and basic ratings.
Eligible aircraft generally include the Cirrus SR series, Diamond DA40, newer Cessna 172/182, Piper Archer, and Columbia 350/400 - newer airframes with modern avionics; older airframes are outside this expansion.
Before binding any policy, ask your broker whether training is a coverage requirement or merely a pricing credit - the distinction is meaningful.
The broader trend toward training-linked underwriting, validated by real loss data, is the more important story behind this announcement.