The 10 Most Expensive Aircraft Insurance Mistakes I've Seen After Helping With More Than 22,000 Aircraft Policies

By Caleb Winterburn

When most pilots think about aircraft insurance claims, they picture dramatic accidents or severe weather. While those certainly happen, the reality is that many of the largest financial losses begin with a simple mistake. A missed detail during a renewal. A misunderstanding about coverage. An aircraft insured for the wrong value. A maintenance issue that turns into a six-figure repair.

After nearly 15 years in aviation insurance and helping with more than 22,000 aircraft insurance policies across Canada, I've learned that the biggest claims are often the ones no one expected.

I've spoken with owners after propeller strikes, hangar fires, wildlife collisions, gear-up landings, forced landings, storm damage, and liability claims worth hundreds of thousands of dollars. Every claim is different, but the lessons are remarkably similar.

My goal isn't to scare anyone. It's to help you avoid becoming the next expensive lesson.

1. Underinsuring the Aircraft

This is the mistake I worry about the most because it is completely preventable.

Many owners try to reduce their premium by lowering the insured value of their aircraft. On paper it seems logical. If the airplane is insured for less, the premium is lower.

Unfortunately, that's not how a serious loss works.

Imagine your aircraft is worth $100,000 but you insure it for only $20,000. If it is declared a total loss, the insurer may pay up to the insured value and then take ownership of the damaged aircraft. You receive $20,000, not the market value.

Saving a few hundred dollars each year can cost you tens of thousands of dollars overnight.

Lesson learned: Always insure your aircraft for a realistic agreed value that reflects today's market.

2. Overinsuring the Aircraft

Many people think insuring an aircraft for more than it's worth provides extra protection.

In reality, it can complicate a claim.

If an aircraft worth $100,000 is insured for $200,000, the insurer will generally investigate whether the aircraft can reasonably be repaired before considering a total loss. The process may take longer because repairing the aircraft could be more economical than paying an inflated insured value.

Insurance is designed to restore your financial position, not create a profit.

Lesson learned: Choose a realistic insured value and review it every renewal.

3. Thinking a Propeller Strike Is "Just a Prop Strike"

One of the biggest misconceptions in aviation is that a propeller strike only damages the propeller.

In reality, many manufacturers require a complete engine teardown following a prop strike. Add a new propeller, labour, inspections, transportation, and downtime, and the repair can easily exceed six figures.

I've seen owners stunned by the final invoice.

Lesson learned: Never underestimate the financial impact of a propeller strike.

4. Forgetting the Gear

Every pilot knows someone who has landed with the landing gear retracted.

Fortunately, these events are often survivable.

Unfortunately, they are rarely inexpensive.

Even a smooth gear-up landing can damage the propeller, engine, belly skins, antennas, avionics, paint, and structural components.

What appears to be a relatively minor event can quickly become one of the largest claims of the year.

Lesson learned: Use checklists consistently and never rush the landing phase.

5. Believing the Biggest Risk Happens in the Air

Some of the largest claims I've seen happened while the aircraft wasn't flying at all.

Hangar fires, windstorms, hail, flooding, and ground handling accidents have destroyed aircraft sitting safely on the ramp.

Sometimes multiple aircraft are involved, multiplying the financial impact.

Lesson learned: Good insurance protects your aircraft whether it's flying or parked.

6. Ignoring Weather

Canada produces some incredibly beautiful flying days.

It also produces violent windstorms, hail, freezing rain, and rapidly changing conditions.

I've seen tied-down aircraft overturned, wings damaged beyond repair, and hangars heavily damaged after storms.

No pilot plans to fly into severe weather, but weather doesn't always ask permission.

Lesson learned: Proper tie-down procedures and appropriate insurance work together to protect your investment.

7. Assuming Wildlife Only Means Birds

Bird strikes receive plenty of attention.

Ground wildlife often doesn't.

Deer, coyotes, and other animals have caused substantial damage during takeoff and landing.

These accidents happen in seconds and frequently result in expensive repairs.

Lesson learned: Stay alert during taxi, takeoff, and landing, especially around dawn and dusk.

8. Forced Landings Are About More Than Flying Skill

Pilots train extensively for engine failures.

Very few expect to experience one.

I've seen forced landings where the pilot did everything right, protected everyone on board, and still ended up with a heavily damaged aircraft.

The success wasn't measured by the airplane.

It was measured by everyone walking away safely.

Lesson learned: Insurance can replace aircraft. It cannot replace lives.

9. Ground Handling Accidents

Many owners focus on flying risks while overlooking what happens around the hangar.

Tow bars disconnect.

Aircraft roll away.

Fuel trucks strike wingtips.

Vehicles clip horizontal stabilizers.

Maintenance equipment damages propellers.

These claims occur more often than many people realize.

Lesson learned: Slow down around aircraft. Most ground accidents happen during routine operations.

10. Choosing the Cheapest Policy Instead of the Right Policy

This may be the biggest mistake of all.

Price matters.

I work hard every day to help pilots find competitive premiums.

But coverage matters even more.

The cheapest policy isn't always the policy you'll be happiest with after a claim.

Ask questions.

Understand your deductibles.

Review your liability limits.

Know what your policy excludes.

Insurance should be evaluated on value, not simply price.

Lesson learned: The best insurance policy is the one that responds the way you expect when your worst day arrives.

Final Thoughts

After helping with more than 22,000 aircraft insurance policies, I've learned that insurance is about much more than paperwork.

It's about protecting dreams.

For many owners, their aircraft represents years of saving, training, and sacrifice. A single unexpected event can change everything.

The good news is that many of the biggest losses I've seen could have been reduced or even avoided through proper planning and the right insurance advice.

Before your next renewal, ask yourself these questions.

Is my aircraft insured for its current market value?

Do I understand what my policy actually covers?

Would I know who to call if I had a claim tomorrow?

If you hesitate on any of those questions, now is the time to review your coverage.

I'd much rather help someone prevent a problem than try to solve one after a loss has already occurred.

Ready to Review Your Aircraft Insurance?

Whether you fly a Cessna, Piper, Beechcraft, Diamond, Cirrus, Mooney, Aviat, Van's RV, a helicopter, floatplane, warbird, or another aircraft, having the right coverage matters.

Request your quote today through Covalen:

https://covalen.ca/en/aviation_insurance_quote

You can also explore more aviation insurance articles, buying guides, and educational resources at https://calebwinterburn.ca.

About the Author

Caleb Winterburn is Vice President of Aviation Insurance at Covalen, a commercial airplane and helicopter pilot, and has helped with more than 22,000 aircraft insurance policies across Canada. He is passionate about helping Canadian pilots better understand aviation insurance before they ever need to make a claim. Through educational articles, presentations, and industry involvement, his goal is to make aircraft insurance easier to understand for every aircraft owner.