[BUG] Double-charged after Max 5x plan silently downgraded to Free mid-cycle

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?

Note: This is a subscription billing issue rather than a CLI tool bug, but I'm filing here because my support ticket submitted 15+ days ago has received no response. Several similar billing issues have been filed in this repo previously (#44726, #50994, #57837), so I'm following that precedent.

My paid Max 5x subscription was silently downgraded to the Free plan only 7 days into a fresh 30-day billing cycle, forcing me to re-purchase the same plan to continue working. This resulted in two charges covering overlapping time periods.

Timeline (KST)

| Date | Event |
|---|---|
| 2026-04-30 | Auto-renewal payment failed → subscription auto-canceled |
| 2026-05-04 | Re-subscribed to Max 5x — payment successful, plan active, cycle should run until ~2026-06-04 |
| 2026-05-11 | Plan unexpectedly reverted to Free with ~24 days of paid time remaining. No prior notification email, no in-app warning, no refund |
| 2026-05-11 | Forced to re-purchase Max 5x to restore access → second charge for an overlapping period |
| 2026-05-22 | Filing this issue. Original support ticket: no response after 15+ days |

<img width="812" height="1053" alt="Image" src="https://github.com/user-attachments/assets/9e407baa-c7c4-435f-9d05-bf63702a56f6" />

<img width="1440" height="3243" alt="Image" src="https://github.com/user-attachments/assets/231bba24-1dc0-4358-8ab4-d4563430993b" />

<img width="812" height="1053" alt="Image" src="https://github.com/user-attachments/assets/e4192a84-114a-42eb-8436-0b50ba46de99" />

<img width="1440" height="3390" alt="Image" src="https://github.com/user-attachments/assets/78ff9380-1df7-485f-bb9c-a19e3d8958a3" />

What Should Happen?

After a successful payment on 2026-05-04, the Max 5x plan should have remained active for the full 30-day billing cycle (until ~2026-06-04).

A paid, active subscription should not silently downgrade to Free mid-cycle. At minimum:

1. The user should be notified before any plan change
2. The remaining paid period should be honored, OR
3. A prorated refund should be issued automatically when the plan changes

Currently, the user has paid twice for overlapping coverage and lost access to a paid service mid-cycle without notification.

Error Messages/Logs

No CLI error messages — this is a billing/subscription state issue, not a runtime error.

Observed in account billing UI on 2026-05-11:
- Plan status displayed as "Free" despite active paid subscription from 2026-05-04
- No downgrade notification received via email
- No system notification shown in claude.ai or Claude Code

Steps to Reproduce

This is a billing state issue rather than a reproducible runtime bug, but here is the exact sequence that triggered it:

1. Have an active Max 5x subscription with a recurring payment method
2. Allow an auto-renewal to fail once (e.g., 2026-04-30 in my case) — subscription auto-cancels
3. Within a few days, re-subscribe manually to Max 5x using the same account (2026-05-04 in my case) — payment succeeds, plan shows active
4. Wait ~7 days
5. Observed: Plan silently reverts to Free despite the fresh paid cycle still having ~24 days remaining

Likely root cause (guess): the system may have treated the new 2026-05-04 subscription as a continuation of the canceled 2026-04-30 cycle rather than a fresh 30-day cycle, causing premature expiration on the original cycle's would-be renewal date.

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.146 (Claude Code)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

Account Info

• Account email: [본인 이메일 주소]
• Region: South Korea (KST timezone)
• Payment method: [예: Visa ending in 1234]
• Existing support ticket ID: [티켓 번호 — 있으면 적고, 없으면 "Submitted via support form on YYYY-MM-DD, no response yet"]

Payment Receipts

• 2026-05-04 charge: Receipt # [2638-6022-6009] — amount: $100
• 2026-05-11 charge: Receipt # [2519-6238-2542] — amount: $110
• (Screenshots of both Anthropic receipt emails attached below, card numbers masked)

What I'm Requesting

1. Refund for one of the two overlapping charges (the 2026-05-04 charge is preferred since access was lost mid-cycle)
2. Root cause explanation: why does a paid plan revert to Free mid-cycle after a prior failed-renewal event?
3. Escalation to the billing team if this isn't the right venue, with a direct contact channel so I'm not stuck waiting on the unanswered support ticket

Suggested Fix (for engineering)

When a user re-subscribes after a canceled cycle, the new subscription should start a fresh billing period from the new payment date — not inherit the expiration date of the previously canceled cycle. If the current behavior is intentional, it should be clearly disclosed at the point of re-purchase.