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Dawn Nelson’s trip to Oaxaca, Mexico, for the Day of the Dead celebrations should have been memorable.

And it was — but for all the wrong reasons.

Her hotel stay, which she’d paid for in advance through Booking.com, was cancelled. She booked another one, which was cancelled again.

Booking.com promised to cover the difference between her original hotel room and the replacement she had to book. Instead, it followed her for weeks, repeatedly asking her for the same paperwork.

Now she’s stuck in a loop.

“I keep getting repeated requests for the same duplicate information without any progress in resolving this matter,” says Nelson. “Can you help me get a refund?”

Nelson’s experience raises a few key questions. What is Booking.com’s responsibility when multiple hotel reservations are cancelled? What steps should you take when a refund request hits a dead end? And how can you ensure that a travel company fulfils its reimbursement promise?

And will Nelson ever get the extra $2,948 she had to spend on her hotel in Oaxaca?

First, let’s find out what happened to her.

“I am beyond frustrated”

Nelson had booked and prepaid her initial hotel reservation over a year ago through Booking.com for a trip to Oaxaca. Late October, when they celebrate Day of the Dead, is one of Oaxaca’s busiest times of the year.

But her hotel cancelled the reservation in February because of a double booking. (It’s unclear if this was the hotel’s or Booking.com’s fault.)

Since there was plenty of time, Nelson made a second reservation through Booking.com. The online travel agency agreed to reimburse her for any cost difference between the first and second bookings.

But the second booking didn’t stick, also because it was a double booking. In April, the second hotel cancelled her reservation.

Nelson spoke with a Booking.com supervisor named Michael, who assured her the company would cover any cost difference if she booked a third hotel.

So she did. And this one worked. But the cost was significantly higher. She spent an additional $2,948 on her accommodations.

After her trip, Nelson submitted a reimbursement request to Booking.com, including all requested documentation. Booking.com kept asking for more information and details, such as screenshots of her bank account. Nelson fulfilled all the requests, but then Booking.com asked her for the same information again.

“I am beyond frustrated,” she says. I have 34 pages of correspondence, email, and chats with the customer service team detailing their numerous requests for documentation, including invoices and credit card receipts. I have faithfully complied with all of them.”

What is Booking.com’s responsibility if a hotel reservation is cancelled?

Here’s the first problem: Booking.com sees itself as nothing more than an intermediary between you and the hotel. So when a booking is cancelled, it keeps its distance:

“Because a partner company facilitates this booking, the property may be overbooked,” it says on its site. “If that’s the case, the partner will notify us. Next, we’ll refund and cancel your booking.

Booking.com says the refund process can take 7 to 10 days and depends on your bank.

But what if you’ve prepaid for your room? Absent an agreement from Booking.com to cover your expenses, Booking.com would owe you a refund, and no more.

Why should Booking.com agree to cover the cost of a new hotel? Because it’s the right thing to do. You might get a low rate if you make a hotel reservation a year in advance. But a few weeks before a big holiday like Day of the Dead, hotel rates will be significantly higher.

Booking.com makes the rules, but it can also change the rules. So if a company like Booking.com agrees to cover your expenses, you can hold it to that agreement.

But what if it refuses to pay?

What steps should you take when a refund request hits a dead end?

A look at the pages upon pages of correspondence shows that Nelson had hit a dead end—and hard.

Booking.com asked her for receipts, which she sent.

Then it asked for bank statements.

Then it tried to contact the hotel for verification, but contacted the wrong hotel.

And then it asked Nelson for screenshots of her bank and credit card statements.

Around and around they went until Nelson was at her wits’ end.

“I feel I have given you all you’ve requested and more,” she texted Booking.com. “Please let me know what is holding up my refund.”

The response?

“Someone will get back to you in 24 hours.”

But no one did. It took days for her to extract another response, which was a request for even more documentation.

What should have happened? Oh, that’s easy. If Booking.com promises you a refund of $2,948, you should get it. The company should handle all the paperwork, not you.

If I didn’t know any better, I’d say Booking.com was trying to get out of paying Nelson.

The workaround: Steady pressure.

Keep all of the text messages, credit card receipts and emails.

Apply steady pressure to get the refund processed.

Escalate your case to a supervisor at Booking.com.

Nelson tried to do all those, including writing a brief, polite email to one of the company’s executives.

The answer? Silence.

How can you ensure that a travel company fulfils its promise of reimbursement?

I’ve reviewed Nelson’s text messages with Booking.com several times. I’m not sure how many of the customer service representatives were people or chatbots, but I suspect most of them were some form of artificial intelligence—and I use the term “intelligence” loosely here.

She was caught in a loop. If I had to guess, Booking.com kept asking for more information in the hopes that she wouldn’t have it and it could deny her claim. But Nelson was smart; she kept all her records and had a ready answer for each request.

So, is there a way out?

When a company makes a promise, it needs to be in writing. As I look at Nelson’s paper trail, I see representatives agreeing to process a refund. But there’s no initial written agreement, which would have been ideal.

Always get an agreement like that in writing — never by phone.

A written agreement is like gold: It’s the company’s guarantee that it will refund the price difference.

But once you’ve started the process of applying for a refund, is there a way to speed it up?

Nelson tried by appealing her case to a Booking.com executive. After that, her next stop was either small claims court — or a consumer advocate.

Small claims court is tedious; even if you win your case, you might have difficulty collecting your judgment. In this case, the advocate was an easier path. And it was the right one.

Not an easy case

This Booking.com case wasn’t easy. It looks like there was a lot of confusion on the company’s side, given that two hotels had cancelled Nelson’s reservation before she found a third. Reviewing her correspondence, it also looks like AI—or, at the very least, employees who did not have a firm grasp of the English language—also played a part.

Nelson reached our advocacy team, and Dwayne Coward reached out to Booking.com.

“For this particular case, the customer experienced cancellations for two hotel reservations due to issues with the properties,” a Booking.com representative told us. “After securing an alternative accommodation, our team worked closely with the customer to ensure the matter was addressed. We have since processed a reimbursement to cover the price difference between their original booking and the alternative property.”

Nelson received a full refund.