[Billing Bug] Two successful payments (Max 20x + Pro) not activating — account stuck on Free tie

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?

I have made two separate successful subscription payments (Max 20x on July 27, 2026, and Pro on August 2, 2026), and both charges were confirmed as processed. However, in both cases my account's plan status remains stuck on "Free" tier instead of reflecting the paid plan. Support's AI agent (Fin) confirmed both payments processed successfully and that my account's internal subscription status shows as "canceled," but could not explain why or fix it, and stated it has no ability to manually activate subscriptions or escalate to a human team.

What Should Happen?

After a successful payment is processed, my account should be upgraded to the corresponding paid plan (Max 20x or Pro) and reflect that plan immediately in Settings > Billing and across the account, with full access to that plan's usage limits and features. A "Resubscribe" option should also appear if the subscription is genuinely in a lapsed/canceled state needing manual reactivation, but this button never appeared for me despite the described "canceled" status.

Error Messages/Logs

Steps to Reproduce

1. Log into claude.ai with an existing account.
2. Go to Settings > Billing and subscribe to a paid plan (in my case, first Max 20x, later Pro).
3. Complete payment successfully (confirmed via invoice/receipt and card charge).
4. Return to Settings > Billing or the account/plan page.
5. Observe that the account still shows as Free tier, with only an "Upgrade Plan" option visible (no "Resubscribe" button).
6. Refresh the page, log out, clear browser cache/cookies, and log back in — issue persists.
7. Wait several hours/days for potential backend sync — issue still persists.
8. Repeat the entire subscription + payment process with a different plan (Pro) — same failure occurs again.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.169 (Claude Code)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

_No response_