Do You Always Need a Flight Instructor for an Insurance Checkout? The Answer Might Surprise You.

One of the most common questions I receive from aircraft owners is:

"My insurance company says I need a check ride with a flight instructor. Is that my only option?"

The answer might surprise you.

Not always.

Many pilots assume that if their insurance documents mention a checkout with a flight instructor, there is absolutely no flexibility. In reality, that requirement is often a starting point rather than the only solution.

Every situation is different, and sometimes there are other acceptable ways to satisfy the insurer's concerns.

Why Do Insurance Companies Require Checkouts?

Insurance companies aren't trying to make flying more difficult.

Their goal is simple.

They want to reduce the chance of an accident when a pilot transitions into an unfamiliar aircraft.

A pilot moving from a Cessna 172 into a Beech Bonanza, Piper Malibu, tailwheel aircraft, floatplane, amphibious aircraft, or Robinson helicopter faces a different level of risk than someone with hundreds of hours on that exact make and model.

The checkout requirement is designed to build experience before a pilot flies independently.

A Flight Instructor Isn't Always the Only Answer

This is where working with an aviation insurance specialist can make a real difference.

Many insurance policies contain standard wording requiring instruction from a qualified flight instructor. However, depending on the pilot, aircraft, location, and circumstances, there may be other acceptable options.

For example, an insurer may consider:

• A commercial pilot with significant make and model experience.

• A previous owner who has extensive experience operating that aircraft.

• A factory-approved mentor pilot.

• Another experienced pilot who can demonstrate the knowledge and experience

the insurance company is looking for.

The important point is this.

Don't assume the answer is no.

Ask.

Every Situation Is Different

Imagine you've just purchased a rare aircraft.

Perhaps there isn't a flight instructor anywhere nearby who teaches on that make and model.

Or maybe you're buying an aircraft in a remote community where instructor availability is extremely limited.

Rather than giving up or assuming you can't meet the insurance requirements, your aviation insurance broker may be able to discuss practical alternatives with the insurance company.

We've helped pilots find solutions in situations where a traditional checkout simply wasn't practical.

Why Your Broker Matters

One of the biggest misconceptions about aviation insurance is that every requirement is set in stone.

In many cases, underwriters simply want confidence that you're capable of safely operating the aircraft.

A knowledgeable aviation insurance broker understands:

• What the underwriter is trying to accomplish.

• Why the requirement exists.

• When an alternative may be reasonable.

• How to present your experience so the insurance company can make an informed decision.

Sometimes the answer will still be that a certified flight instructor is required.

And that's okay.

Safety always comes first.

But other times, there may be another path that satisfies both the insurer and the pilot.

Where There's a Will, There's Often a Way

One phrase I use often is:

"Where there's a will, there's usually a way."

Insurance isn't simply about reading policy conditions.

It's about understanding the risk, finding practical solutions, and working with the insurance company to achieve the safest outcome possible.

Before assuming you can't meet an insurance requirement, have a conversation with your aviation insurance broker.

You may have more options than you think.

Thinking About Buying an Aircraft?

If you're purchasing your first aircraft or transitioning into a new make and model, I'd be happy to review your situation before you commit.

Sometimes a quick conversation can save weeks of frustration and help you understand your options before the policy is issued.

If you'd like an aircraft insurance quote or simply want to discuss your transition requirements, visit Covalen's Aircraft Insurance Quote Page or contact me directly. The earlier we become involved, the more options we often have.

COPA Aviation Insurance Canada | ACIP Program - Covalen

The earlier we become involved, the more options we often have.

If you're unsure whether your experience will satisfy an insurer's transition requirements, let's have that conversation before assuming a flight instructor is your only option. Often, there are solutions worth exploring.

About the Author

Caleb Winterburn is Vice President of Aviation Insurance at Covalen and a commercial airplane and helicopter pilot.

Having worked with thousands of aircraft insurance policies across Canada, he helps pilots understand aviation insurance requirements and find practical solutions that keep them properly protected.

Through his educational articles, videos, and presentations, Caleb's goal is to make aviation insurance easier to understand for pilots across Canada.

For more aviation insurance tips or to request a quote, visit or connect with Caleb on LinkedIn.