We thought we had done everything right. We compared plans, bought a policy through InsureMyTrip, kept every receipt, and filed the moment the trip went sideways. Eighteen days later, IMG approved the full amount we claimed. What followed took months.
This started on a trip from Hawaii. The disruption came later in the journey, on a South Pacific flight segment from Rarotonga to Papeete. We left to visit French Polynesia and the Cook Islands, and one broken link (or aircraft engine in this case) knocked the whole chain that followed.
The flight that caused the problem was on Air Rarotonga.
When the plane had an engine issue, the flight was canceled, and suddenly we were stuck for an extra day and night in Rarotonga, with last-minute hotel, meals, and transportation costs we hadn’t planned for. Not only that, but we also lost a prepaid night in Papeete and the car rental tied to that arrival.
How IMG handled the claim.
We filed the claim on January 1. By January 19, IMG approved the full $744.72. Zero was marked ineligible. Zero was disputed. Their own determination broke the claim into four line items covering the travel delay and trip interruption expenses for both claimants.
Reseller sites advertising IMG plans say claims are often settled in under 30 days on average. Our claim was approved within that window. The problem was what happened after approval. Why did the money stop?
IMG distributed the money in fragments without paying in full.
First, Rob got a direct deposit of $125. After that came a long stretch of nothing. Almost two months later, and after complaining, a check arrived for $484.60. That brought the total we had actually received to about $609.60, compared with the $744.72 already approved. Months after IMG said the claim was settled, we are still short more than $135. Which isn’t even the point here.
At first, this looked like a slow reimbursement process; then it stopped making sense entirely. This was not a giant claim, not disputed, not denied, already approved in full very rapidly. Yet the money came in fragments, with gaps and complaints in between, long enough to make you wonder if the rest was ever coming.
Plenty of travelers would probably stop after the first partial payment or the first round of emails that go nowhere. At some point, the remaining balance is not worth the time, and we understood that. We kept pushing because once a company tells you in writing that it owes you money, it should not become a months-long chase to collect it. We became curious, and still are.
Where the insurance broker came in.
The company you buy through and the company that provides the coverage and handles the claim are often different. You shop through a marketplace like InsureMyTrip or Squaremouth because they make it easy to compare plans, but the policy is actually issued by a separate insurance company.
In our case, InsureMyTrip became the difference between movement and no movement. We have gone back to them repeatedly as the payments stalled, and each time they pressed IMG on our behalf. More money came after that.
We found public complaints against IMG that sounded uncomfortably familiar.
In a January 2026 Rick Steves forum thread, a traveler said an IMG claim remained unresolved after more than three months and that the broker Squaremouth was investigating, while another poster described a similar experience. The original poster later said IMG agreed to settle only after an appeal to Squaremouth and a public review campaign.
Trustpilot reviews describe other long-running IMG claim disputes, including one reviewer who said a claim had been unresolved for seven months. The details vary, but delay, confusion, and outside pressure show up more than once.
We have bought travel insurance through brokers, through comparison marketplaces, and directly from insurers over the years we’ve published and traveled for Beat of Hawaii. There’s never been a problem like this. The policy coverage was only part of the value; the other part was having someone help when the agreed-upon payment didn’t arrive.
What we would do differently now.
We would be much more inclined now to buy only through a broker or marketplace that has an actual support role when claims go sideways. The policy looked fine going in, and the problem showed up on the way out.
We would also spend more time looking into who actually stands behind the policy and what other travelers have experienced once claims are filed. Most people do not shop that way. They compare coverage, price, cancellation rules, and medical terms. They do not usually assume they need to investigate what happens after a claim is approved. After this trip, we do.
If you are buying insurance for an expensive trip out of Hawaii, it is worth knowing who will still be in your corner when the money does not show up.
Have you ever had to fight to get a travel insurance claim paid, and did buying through a broker make any difference?
Lead Photo: Tunnels Beach on North Shore Kauai.
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The reason for partial payments could be that they sold portions of the policy to other groups or associations. This happened to me years ago on a Lloyds of London policy. It was approved right away and it took almost a year to get the total amount. Upon multiple complaints was told that Lloyd’s get so many policies that they share the risk amongst many groups that take some of the premium as well. When a claim is approved, they only pay as the reinsurance groups pay them.
Insure directly with a highly rated company. We recently had to cancel a trip we’d insured directly with Allianz, booked with Alaska and partner airlines, for medical reasons. They’re paying promptly (but in segments, as you noted).
We don’t often buy travel insurance because the exclusions seem to cover every problem and inconvenience except a true mechanical on aircraft, as you experienced.
AAA paid out 100% quickly on a claim for a road tire incident in the middle of nowhere on a Sunday night. Covered transportation to a town meals, and lodging.
On international trips we used Tokyo Marine. While we didn’t make a claim, we received an email asking if everything went in the trip as expected, and were we satisfied with their service. That was new.
Aloha and thank you for your post. I would like to know what others have used and if they were happy with the outcome. Are travel agents helpful at all or do they just sell you a policy from a company that pays them the most commission? I’ve never purchased travel insurance for my many years of traveling to Hawaii, but I’m looking into now for my next trip. Thanks all.
I would like to know if anyone has been paid for car rental damage using the Costco $6.00 a day plan? I think Zurich is the provider? What about the Costoc Citibank card coverage?
Don’t know about the Citi card but the Chase United Explorer card provides full coverage for accident damage. Doesn’t rope in your personal car insurance carrier so no spike in premium after an accident.