u/Alarming-Director500

Has anyone successfully resolved a ChatGPT Plus / Apple ID subscription loop issue?

I’ve been stuck in this for weeks and support has not resolved it.

What happened:

• I originally subscribed to ChatGPT Plus through Apple billing.
• I later had account/login confusion involving Apple login vs email login.
• I intentionally waited until May 20 for the prior subscription/account state to cancel so I could start fresh.
• After that, I attempted to subscribe again using my personal Gmail.
• The system immediately told me: “Purchases for your Apple ID are associated with another ChatGPT account.”
• When I log in with “Continue with Apple,” it now says I already have an active Plus subscription renewing June 22, 2026.
• But I still can’t clearly restore/access the correct paid account state.

At one point support also asked whether the issue could be tied to my work/enterprise account email, which makes me think there may be some kind of account-linkage or identity overlap happening behind the scenes.

Support told me my case was escalated on May 19, but I still have no actual resolution.

I’m trying to understand:

1. how to identify which account the Apple subscription is actually attached to,
2. whether anyone else has successfully untangled this,
3. and whether there’s an actual human escalation path that works.

I’m honestly exhausted from spending hours looping through login/subscription flows.