I have a second email I've not used for some time and Can't log in

Hey Jodi, I completely get the frustration. Getting trapped in an automated recovery loop when you just need to unlink an old address from your iPhone is incredibly maddening.

As someone who works extensively with cross-platform authentication architectures, here’s the reality of the situation: Microsoft's Automated Account Recovery (ACSR) system relies heavily on server-side metadata (like sent emails, subject lines, or IP history). Since your inbox is effectively a ghost town, the algorithm will structurally reject your requests. Microsoft support agents are actually systemically restricted from manually overriding this protocol for security reasons.

However, your core goal isn't really recovering the email—it's unlinking it from iMessage. You can bypass the Outlook recovery entirely by tackling this from the Apple side:

Force-Remove via Web Portal: Go to appleid.apple.com on a desktop browser. Log in with your primary Apple ID. Navigate to Sign-In and Security > Email & Apple ID. You can usually delete the inactive Outlook alias directly from here without needing an OTP from the Outlook inbox.

Deregister iMessage Remotely: If the device itself is stubborn, use Apple's portal at selfsolve.apple.com/deregister-imessage to sever the connection at the server level.

Microsoft "Human" Routing: If you absolutely must speak to a Microsoft rep, avoid the "Account Access" prompts. Go to support.microsoft.com/contactus, type "Talk to an agent," and categorize your issue under Billing. Financial queues are prioritized for live human agents who can sometimes escalate account locks internally.

Hope this unblocks you. Let me know if the Apple-side bypass does the trick!