OpenAI offered me 100% off ChatGPT Plus to stop me cancelling, charged me twice, then spent 6 weeks trying to explain why.

[u/balamir]

I genuinely cannot believe how much effort OpenAI has put into avoiding a straightforward £16.67 billing issue.

And at this point, it's not even about the money anymore.

Here's what happened:

August 2026 - I tried to cancel ChatGPT Plus.

While cancelling through the Codex desktop app, OpenAI presented me with a retention offer: 100% off Plus for one month if I kept my subscription.

I clicked "Claim Offer" and decided to stay.

My Billing page subsequently displayed:

"You've got 100% off Plus."

Great, right?

8 September — Charged £16.67 anyway.

I contacted support, explaining that I'd accepted the retention offer specifically because I was about to cancel.

What followed was weeks of back-and-forth with multiple support agents.

Some asked me for a promotional code. There wasn't one. It was literally OpenAI's own retention offer displayed during cancellation.

Others couldn't verify when the discount should apply.

Eventually, they told me the September charge couldn't be refunded because the discount was actually scheduled for October.

27 September — OpenAI explicitly confirmed October would be free.

Their support representative wrote:

"No additional action is required from you to keep the currently displayed promotion. Your Plus subscription remains active, and the promotional benefit is associated with the next billing period beginning October 8, 2026."

Finally, a clear answer. I had it in writing.

8 October — Charged another £16.67. Seriously?

Despite the explicit written confirmation, OpenAI charged me again.

Even better? My Billing page STILL displayed "You've got 100% off Plus."

Except now the discounted renewal date had mysteriously moved to 8 November.

So apparently my free month just keeps moving into the future while the payments keep coming.

I contacted support again.

Their AI assistant offered me two options:

1. Request a refund, which would normally terminate my Plus access.
2. Investigate the missing discount while keeping my subscription active.

Why should I have to lose my subscription to get back money that shouldn't have been charged in the first place?

I requested escalation.

Another support agent acknowledged that the September 27 confirmation directly contradicted the October charge. However, they couldn't manually correct the promotion, couldn't guarantee November would be free, and couldn't offer a concrete resolution.

So I asked for a proper investigation.

Then came the "next level of Support".

After more than six weeks of explaining the same situation, someone called Errizz replied, saying they'd reviewed my account.

Their conclusion?

They could only find a promotion recorded on 9 December 2025 and couldn't identify my August 2026 retention offer.

Then they asked me to provide:

• A screenshot of OpenAI's own September 27 email confirming October would be free.
• A screenshot of the retention offer shown during cancellation in August.

They were literally asking me to provide proof of an email their own support team sent me, which was already part of the support case.

And the retention offer? Who takes screenshots of every cancellation screen just in case the company later claims it cannot find its own promotion?

Meanwhile, my Billing page had been explicitly confirming that I had 100% off Plus.

Apparently, that wasn't enough either.

The ridiculous part? All of this is over £16.67.

Think about it.

Multiple support representatives, repeated investigations, contradictory explanations, weeks of emails, escalations, requests for evidence already provided, and absolutely no resolution.

The time I've spent dealing with this is worth considerably more than the disputed amount.

And here's the irony:

I WAS ALREADY CANCELLING MY SUBSCRIPTION.

OpenAI convinced me to stay by offering a free month.

They then charged me in September, promised October would be free, charged me again in October, and eventually claimed they couldn't find the offer.

I didn't ask for anything special. I just expected them to honour the offer they presented and subsequently confirmed in writing.

I've now decided to cancel ChatGPT Plus. I'm not interested in wasting another minute going back and forth with their support team.

I'm posting this because I think people should know what can happen when accepting one of these retention offers.

And the most frustrating part isn't the money. It's how little accountability there seems to be when their own billing system and support team contradict each other.

I have the billing screenshots, invoices and written support confirmations to back this up.

Has anyone else experienced something similar with ChatGPT Plus retention discounts, or had a promotional offer that kept getting pushed to the next billing cycle?

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[u/Outrageous-Toe-2048]

So you were about to cancel, OpenAI offered you a free month to keep you subscribed, charged you anyway, and then spent six weeks trying to figure out an offer they made themselves? What the actual fuck.

The most absurd part is that they confirmed the discount in writing, your billing page still showed 100% off, and somehow they couldn't find their own promotion. Then they asked you to prove an email their own support team had sent you. You couldn't make this shit up.

I've dealt with OpenAI support myself, and the endless back-and-forth with different agents sounds painfully familiar.

All this over £16.67, and they ended up losing the customer they were trying to retain. Brilliant business strategy.

[u/balamir → u/Outrageous-Toe-2048]

Exactly! That's what makes the whole situation so ridiculous. They offered the discount to stop me from cancelling, then managed to give me even more reasons to leave.

And the worst part isn't even the £16.67 anymore. It's the amount of time wasted going back and forth with support agents who either don't read the previous conversations or completely ignore the evidence.

All they had to do was honour their own offer. Instead, they've turned a simple billing issue into a six-week circus :)

[u/Equal_Tradition_5420]

HOLY sam GOING CRAZY lol... RIP man...