[BUG] Claude Pro → Max upgrade bug forced ~$587 in unwanted extra credit charges — financial damage caused by Anthropic's server-side failure

Preflight Checklist

• [x] I have searched existing issues and this hasn't been reported yet
• [x] This is a single bug report (please file separate reports for different bugs)
• [x] I am using the latest version of Claude Code

What's Wrong?

<img width="794" height="944" alt="Image" src="https://github.com/user-attachments/assets/e8e16951-871d-4be0-8f4d-d522253c5ae9" />
<img width="909" height="1025" alt="Image" src="https://github.com/user-attachments/assets/d286f871-051a-4eba-bd59-177b00e050da" />
<img width="663" height="774" alt="Image" src="https://github.com/user-attachments/assets/227316c7-59f1-48fa-ac28-32a21bff2e26" />

What Should Happen?

[BUG] Pro → Max upgrade bug forced ~$587 in unwanted extra credit charges — financial damage caused by Anthropic's server-side failure

Preflight Checklist

• [x] I have searched existing issues and this is related to #57122, #55982, #55917
• [x] This is a billing damage report caused by the confirmed upgrade bug

---

What's Wrong?

Due to the confirmed Pro → Max upgrade payment bug (see related issues), I was completely unable to upgrade my plan despite multiple attempts over two days. As a result, I was forced to remain on the Pro plan and consume extra usage credits to continue my work.

This resulted in US$586.81 in extra credit charges within approximately 48 hours — a cost that would have been entirely avoided had the Max upgrade functioned correctly.

Steps to Reproduce

1. Log in to claude.ai on an active Pro subscription
2. Navigate to Settings → Billing
3. Select Max plan and enter payment details
4. Receive 'Payment failed. Please try again later.' on every attempt
5. Be forced to continue on Pro plan, consuming extra credits at high cost

Expected Behavior
Upgrade completes successfully. User pays Max plan fee (~$100/month) and receives adequate usage capacity.

Actual Behavior
Upgrade fails every time due to Anthropic's server-side bug. User is trapped on Pro plan and forced to pay $586.81 in extra usage credits over 48 hours to maintain workflow.

Financial Impact

• Extra credits charged: US$586.81
• Monthly cap set: US$800
• Timeframe: May 10–11, 2026
• If Max plan had worked: would have paid ~$100 total

Evidence

• Usage dashboard screenshot showing $586.81 charged
• Related GitHub issues confirming this is a known server-side bug
• Anthropic support was contacted but only provided generic card-check responses

Request
I am requesting that Anthropic:

1. Acknowledge this as a confirmed billing bug that caused direct financial harm
2. Refund the extra credit charges incurred as a result of the upgrade failure
3. Fix the Pro → Max upgrade payment flow immediately

Note: A similar billing bug (Hermes.md detection bug) was previously resolved with refunds + one month credit after community visibility. I am requesting the same accountability here.

Region: South Korea
Plan: Claude Pro ($20/month)
Browser: Tested on multiple browsers

Error Messages/Logs

Payment failed. Please try again later. If the problem persists, contact support at https://support.anthropic.com/

Steps to Reproduce

1. Log in to claude.ai with active Pro subscription
2. Navigate to Settings → Billing
3. Select Max plan upgrade
4. Enter payment details (card info, billing address — all correct)
5. Click confirm — receives "Payment failed. Please try again later."
6. Repeated attempts over 2 days — same error every time
7. Forced to remain on Pro plan and consume extra usage credits
8. Result: $586.81 charged in extra credits within 48 hours

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.138

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

This is a billing damage report. Due to Anthropic's server-side upgrade bug, I was financially forced to spend $586.81 in extra usage credits over 48 hours.

Related confirmed issues: #57122, #55982, #55917

Screenshots attached:

• Usage dashboard showing $586.81 charged / $800 cap
• Failed Max upgrade payment screen
• Billing history

Anthropic support was contacted but only provided generic responses (check card details, check address). This is clearly a server-side issue, not a user error.

Requesting: refund of extra credit charges caused directly by this upgrade bug.

<img width="794" height="944" alt="Image" src="https://github.com/user-attachments/assets/0db7efcf-fa5c-4bd4-9e82-1d581becf545" />
<img width="909" height="1025" alt="Image" src="https://github.com/user-attachments/assets/6b070335-995d-4fab-a065-797cc1415c59" />
<img width="663" height="774" alt="Image" src="https://github.com/user-attachments/assets/268bdf56-c9f7-4b0b-a681-23c290100b98" />