May 2, 2026
One Florida couple's long-awaited trip to Italy never made it past the departure date.
In the weeks leading up to the 11-day vacation to celebrate both her 65th birthday and the Catholic jubilee year, Diane Dembinski unexpectedly injured herself. "I lifted our grandson and I got hurt," she told Tampa Bay 28 (1).
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She and her husband, Robert, filed a medical claim with their travel insurance company — complete with a doctor's note stating that Diane had "acute" compression fractures and would be "unable to keep her scheduled trip" — but found their $10,000 claim was denied.
The reason? Terrawind Global Protection, an insurance company based in Mexico, cited Diane's injury as a pre-existing condition due to osteoporosis. Now, if the couple want to pursue the issue, they have to sue in Chile, where the insurance was issued.
What was meant to be a safeguard against exactly this kind of situation has instead turned into a dispute over policy language, exclusions and where — and how — the couple could challenge the decision. "You feel really cheated," Robert said.
Why the 'safety net' failed
The Dembinskis thought they did everything right — they bought insurance, got a doctor's note and filed their claim. But the insurer still said no.
On paper, trip cancellation coverage is meant for exactly this kind of situation: a sudden medical issue that forces you to miss your planned trip. In reality, though, these claims often come down to the fine print — and that's where things can unravel quickly.
In this case, Terrawind Global Protection pointed to a pre-existing condition. Diane's osteoporosis, they argued, meant the injury wasn't fully unexpected under the policy terms. That kind of reasoning can catch a lot of travellers off guard. Many policies don't just look at what happened — they look at your underlying health history and whether it could have contributed.
And this isn't unusual. Some estimates suggest roughly 15%-25% of travel insurance claims are denied or only partially paid (2), often because the situation doesn't line up perfectly with how the policy defines a "covered reason."
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Paperwork is another common hurdle. Missing or incomplete documentation — like medical details, timelines, or supporting records — is one of the biggest reasons claims get rejected. Some estimates suggest it plays a role in up to a third of denials (3).
Medical cancellations, in particular, are tightly defined. It's not enough that something went wrong — it has to meet very specific criteria in the policy. Even small technicalities can make the difference between a payout and a rejection.
For the Dembinskis, the denial was frustrating enough. But what really shocked them was learning they might have to take legal action in another country entirely to challenge it. It's the kind of clause most people don't notice when they buy coverage — until they actually need to use it.
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What to do if your travel insurance claim is rejected
The Dembinskis' case also highlights the possible issues when working with an international insurer. It can make disputes more complicated — and harder to fight if things go wrong.
But if your travel insurance claim gets denied, regardless of location, that doesn't have to be the end of the road. There are still steps you can take — and in some cases, decisions do get reversed.
Ask for the denial in writing: Don't settle for a vague explanation. The insurer should clearly spell out why your claim was rejected and which part of the policy they're relying on.
Revisit your policy: It's certainly a tedious exercise, but it's an important one. Look closely at how the policy defines things like "pre-existing condition," "family member," or "covered reason." These are the little details that will matter down the line.
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File a formal appeal: This is a chance to really strengthen your case. Include anything that might have been missing the first time. Think: more detailed medical records, a follow-up doctor's note (in Diane's case), or other supporting documents.
Escalate if you are not getting anywhere: If the insurer stands by the denial, you may be able to take your complaint to a regulator or ombuds service, depending on where the policy was issued.
Figure out what kind of denial you are dealing with: For example, missing paperwork or unclear details (aka. "soft" denial) can often be resolved. But a denial based on policy wording (a "hard" denial) is tougher — although still worth questioning if something doesn't seem right.
At the end of the day, the process can be slow and frustrating. But knowing how to respond — and what insurers are actually looking for — can give you a better shot at turning a "no" into a second look.
And in the meantime, if you're looking to take on similar coverage, interrogate the fine print ahead of time, to ensure it provides you with the type of coverage you need. Lastly, investigate where you would need to legally contest any claims and whether it makes more sense to stick to an insurer who is based out of the U.S.
Article Sources
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Tampa Bay 28 (1); Jet Set Protect (2),(3)
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Laura Grande is a freelance contributor with nearly 15 years of industry experience. Throughout her career she's written about and edited a range of topics, from personal finance and politics to health and pop culture.
