I’m having the same issue. For a while, I kept seeing the “Join the Apple Developer Program” prompt, but when I tried to enroll, I would get this message: “Your Apple Account is already associated with the Account Holder of a membership.” Now my account says that my membership has expired. However, when I click “Renew Membership,” it just loops me back to: “Sorry, you can’t enroll at this time. Your Apple Account is already associated with the Account Holder of a membership.” I’ve been trying to reach Apple Developer Support but haven’t had any luck so far. Has anyone found a solution to this?