Get full refunds on a non-refundable hotel and flight with a ChatGPT Dot after falling sick

Posted

Sep 29, 2026 by Max Weinbach (@mweinbach)

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Last checked

Oct 22, 2026

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Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

Max Weinbach got a little sick in Hawaii after an 8 1/2 hour flight delay and couldn't face flying to San Francisco for OpenAI's Dev Day. Weinbach had a ChatGPT Dot try to cancel the non-refundable hotel and flight and get refunds. It emailed the hotel, which didn't reply; after 2 days it emailed the general manager, who approved cancellation with no fee. When a $210 charge then appeared on the card, it followed up to ask why. It also sent Delta a request citing the 8.5 hour delay and asking for an exception, and Delta called to say it would approve a full refund.

AI tool

ChatGPT Dots

The source didn't share its exact prompt, so we wrote this from what it describes.

What the prompt labels mean

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Cancel a trip I can no longer take and get as much money back as possible on non-refundable bookings.

What I can give you (ask for whatever's missing):
- The bookings, with confirmation numbers and amounts: [DETAILS]
- Why I can't travel, in a sentence or two: [REASON]
- Any disruption that supports my case, such as delays: [DETAILS]

Rules:
- Write polite, short requests to each company through its official channel, stating the facts and asking for a refund or a fee waiver.
- If there's no reply in a couple of days, follow up or escalate to a manager.
- Check my card for any charges after a cancellation is agreed, and query any that don't match.
- Don't share health details beyond what I approve, and don't accept credit instead of a refund without asking me.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A log of each request, reply and outcome, with reference numbers.

You'll know it worked when: each booking is cancelled and refunded, or I know exactly what's still owed.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Cancel a trip I can no longer take and get as much money back as possible on non-refundable bookings.

What I can give you (ask for whatever's missing):
- The bookings, with confirmation numbers and amounts: [DETAILS]
- Why I can't travel, in a sentence or two: [REASON]
- Any disruption that supports my case, such as delays: [DETAILS]

Rules:
- Write polite, short requests to each company through its official channel, stating the facts and asking for a refund or a fee waiver.
- If there's no reply in a couple of days, follow up or escalate to a manager.
- Check my card for any charges after a cancellation is agreed, and query any that don't match.
- Don't share health details beyond what I approve, and don't accept credit instead of a refund without asking me.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: A log of each request, reply and outcome, with reference numbers.

You'll know it worked when: each booking is cancelled and refunded, or I know exactly what's still owed.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Cancel a trip I can no longer take and get as much money back as possible on non-refundable bookings.

What I can give you (ask for whatever's missing):
- The bookings, with confirmation numbers and amounts: [DETAILS]
- Why I can't travel, in a sentence or two: [REASON]
- Any disruption that supports my case, such as delays: [DETAILS]

Rules:
- Write polite, short requests to each company through its official channel, stating the facts and asking for a refund or a fee waiver.
- If there's no reply in a couple of days, follow up or escalate to a manager.
- Check my card for any charges after a cancellation is agreed, and query any that don't match.
- Don't share health details beyond what I approve, and don't accept credit instead of a refund without asking me.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Tell me the policy or rule each request relies on, and what to try next if it's refused.

Output: A log of each request, reply and outcome, with reference numbers.

You'll know it worked when: each booking is cancelled and refunded, or I know exactly what's still owed.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://x.com/mweinbach/status/2105049222592532581