[BUG] Pro annual payment charged ($199.80) but account shows Free plan — Fin AI unable to escalate/resolve

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?

This is a billing/account entitlement issue, not a Claude Code CLI bug. I am filing here because there is no dedicated billing issue tracker, and normal support channels (Fin AI chat, email) have failed to escalate to a human. I paid $199.80 USD for the Claude Pro annual plan on May 20, 2026. My account currently shows the Free plan instead of Pro, which is also blocking my use of Claude Code CLI since it authenticates via my Pro subscription.

What Should Happen?

My Pro annual subscription should remain active for the full paid period. I am requesting: (1) restoration of Pro access, and (2) an extension of my subscription end date to compensate for the downtime already experienced.

Error Messages/Logs

Steps to Reproduce

1. Purchase Claude Pro annual plan
2. At some point after successful payment, account reverts to Free plan
3. This appears to match a known entitlement-sync bug pattern reported in issues #56895, #66558, #60923, #24235

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

N/A — I cannot run claude --version meaningfully since my account is currently downgraded to Free due to this billing issue

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_