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How One Woman Won $10,000 By Reading Her Insurance Contract

Maggie Overholt

Maggie Overholt


4 min. read

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Pop quiz: What do a Wonka candy bar and a travel insurance policy have in common? Not much — except that if you’re lucky, you might just win big after buying one.

Last month, travel insurance comparison site Squaremouth awarded $10,000 to high school teacher Donelan Andrews, winner of the company’s “It Pays to Read” sweepstakes. The company matched her winnings with a $10,000 donation to literacy advocacy group Reading is Fundamental, and then topped things off by making $5,000 donations to both of the Georgia high schools where Andrews works.

Oh, and did we mention the contest happened completely, 100 percent in secret?

It Can Pay to Read The Fine Print. Literally.

Here’s how it went down: Andrews, celebrating the 25th anniversary of an annual friends’ vacation, recently booked a trip to London. To protect her down payments and travel plans, she purchased a travel insurance policy from Tin Leg — a subsidiary of Squaremouth. Things were looking fairly typical up until this point.

But when Andrews reached page seven of her insurance contract (yes, she sat down to read the whole thing from beginning to end), everything changed.

“If you’ve read this far, then you are one of the very few Tin Leg customers to review all of their policy documentation,” the fine print read. There was more.

“We estimate that less than 1 percent of travelers that purchase a travel insurance policy actually read all of their policy information — and we’re working to change that.”

How? By offering $10,000 to the first person who made it to page seven of their paperwork and contacted the company to collect their winnings. That was all it took.

Donelan Andrews holds a check from Squaremouth at one of the two schools where she teaches, both of which also received $5,000 donations from the company. Image: Squaremouth

Why Did Squaremouth Do It?

Squaremouth’s secret contest was meant to promote the importance of actually reading contracts before you agree to them. Not just for travel insurance, but for any service that requires you to sign away your soul (or at least, your cancellation rights) before buying.

“Our number one goal as a company is saving our customers money. We never want a customer to spend more than they need to on a policy, or to pay for a policy if we know they’re concerned about something that can’t be covered.”

Squaremouth on the “It Pays to Read” contest

In terms of insurance, reading your policy’s fine print will help you understand which specific hazards or events you’re insured against, and which ones you aren’t. That way you won’t end up throwing undercooked spaghetti at the metaphorical claims wall and watching it peel off.

“Over the past 16 years, we’ve learned that many travelers buy travel insurance and just assume they’re covered if anything goes wrong, without actually reading the details of their policy,” says Squaremouth. “However, this often leads to claims for losses that are not covered.”

And if it’s not covered, your insurance company won’t pay. The same goes for homeowners, auto, and other important lines of insurance.

Will Squaremouth Run The Contest Again?

Your guess is as good as ours.

We called Squaremouth to see if we could glean any insider information, but weren’t able to reach the company for comment.

But We Can All Be a Little More Like Donelan Andrews (And We Can Hold Out Hope)

Andrews is among the miniscule group of people that actually. Reads. Every. Page. Before they sign a contract. With a background in consumer economics and a 25-year teaching career in the field, you could almost say it’s in her nature.


Andrews shows shock and joy as Squaremouth presents prize money and donations. Image: Squaremouth

“I always read all the fine print,” Andrews told the Washington Post. “I know I sound like a nerd, but I learned to read contracts so you don’t get taken advantage of.”

It’s hard to imagine an insurer (or any other company, for that matter) catching her off guard.

We don’t know if Squaremouth will ever hide another golden ticket. But we do know that, regardless of cash prizes, it’s worth it to read the fine print on your policy. Especially before you buy. Doing so helps ensure you’re not paying for more coverage that you need — or, worse, paying too much for too little coverage.

Next time you’re shopping for insurance, channel your inner Donelan Andrews and hunker down for a nice, cozy one-on-one with that contract. And if you’re not sure where to begin the conversation, we’ve got some resources to help you out:

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