Hi @Rick Green,
I hope you’re having a great day.
I understand how unexpected and inconvenient it can be to lose access to the “Contact Support” option - especially when you were already working with a support agent and followed their recommendation to clear application data.
To help you continue your support case (Work account on Mac), here are the options available:
Option A: Try restoring the in‑app support entry (if your tenant permits it)
- In Outlook, navigate to Outlook > Preferences (or Settings, depending on your version), then open Privacy.
- Enable Optional connected experiences and Send additional diagnostic and usage data (if available; these settings may be restricted by admin policy).
- Make sure your Outlook client is up to date by selecting Help > Check for Updates to update to the latest supported 16.x build.
- Return to Help > Contact Support and check whether the option appears again.
- If it’s still missing, it is likely disabled by your organization’s admin policies.
Reference: Contact support within Outlook for Mac - Microsoft Support.
Option B: Continue your existing case without the in‑app button
- Reply directly to the original support case confirmation email (the subject line includes your case number). Your reply will be added to the same ticket and your assigned engineer will receive it.
- Alternatively, you can visit Contact Microsoft Support, start a chat or request a callback, and provide your existing case ID so the agent can continue the case on the same thread.
I hope these steps help you get reconnected quickly. Please try them and let me know if the issue persists. I'm here to assist you further until everything is resolved.
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