How to get help from a real human

Question

I need help from a real human. AI does not provide useful answers. I need help with Outlook for Mac. My email keeps reappearing after being deleted.

Answer 1

I tried everything that I was able to try. SI was not able to try some things because the tabs or menu items did not exist.

I tried to see if IMAP was enabled and I found that some of my gmail accounts are not IMAP accounts, they are Google accounts. Google says that all gmail accounts are IMAP accounts now (since 2025) and IMAP is automatically enabled. I don't know how to tell if my account is IMAP enabled because it is a Google account and it does not show me any settings. I don't know how to look at the settings.

I removed and re-added the account from Outlook a couple of times, but the problem has not gone away. I restarted everything but the problem did not go away.

I did not check the recoverable items folder because I don't know what it is or how to access it.

I did not check for duplicates because I don't think I have any third-party apps or add-ins, but I really don't know what this means. What kinds of things is this referring to?

I suspect something is wrong with the accounts that are Google accounts rather than IMAP, but I don't know how to change them to IMAP. When I delete them and re-add them they come back as Google accounts. They are all gmail accounts.

I tried and tried and tried to access "help" from the outlook website. I just kept getting told to log in again, even when I was logged in. The directions from Outlook are very poor and impossible to follow. I used to be able to get help very easily from Outlook, but I haven't needed to for a couple of years.

I feel like terminating my account with Outlook. It is a pain to use .

Answer 2

Hello MooseFoot

Thank you for reaching out to Microsoft Q&A Forum. I understand you want to reach a real person, and the “deleted email keeps coming back” issue can be frustrating.

Just to confirm, have you already tried the steps shown in the Q&A Assist reply under your thread? If yes, what happened?

Could you also let me know when the email "comes back", does it also reappear if you check your mailbox on the web (https://outlook.live.com), or only inside Outlook for Mac?

Besides, Outlook for Mac has an in-app "Contact Support" option (In Outlook for Mac, click Help > Contact Support). If “Contact Support" is missing, Microsoft explains common reasons (version requirements, privacy settings/connected experiences, diagnostics settings). Please see this official guide: Contact support within Outlook for Mac - Microsoft Support

Once you’ve tried the steps above, you can also try to reach out to the Microsoft Support team via a web browser. It may offer live chat and, depending on your subscription/region, an option to request a callback:

• Go to Contact - Microsoft Support
• Type a brief description of your issue in the search box.    
• Click "Get Help", then scroll to the bottom and select "Contact Support”.
• Select the appropriate Products & Services/ Category.
• Look for and select "Chat with a support agent in your web browser" (during business hours) or a similar callback option (if available). Explain your situation clearly.

Thank you for your precious time and understanding.

Answer 3

To get help from a real human for Outlook/Outlook.com and issues with messages reappearing after deletion, use Microsoft’s official support and live chat options.

1. Use Outlook.com in a browser and sign in.
2. Select Help on the menu bar.
3. In the Help pane, type the issue (for example, “emails reappearing after delete”).
4. If self-help articles do not resolve the problem, scroll down and select Yes under Still need help?.
5. Choose Chat with a support agent (or similar) to start a live chat with a human agent in the browser.

If sign-in is not possible, use this link for Outlook.com account access issues: https://go.microsoft.com/fwlink/?linkid=2194326.

For general Microsoft account and subscription issues, use Account & Billing Help: https://go.microsoft.com/fwlink/?linkid=2189071.

If phone support is preferred for other Microsoft products or services, use the customer service phone directory described here: https://support.microsoft.com/en-us/topic/customer-service-phone-numbers-c0389ade-5640-e588-8b0e-28de8afeb3f2.

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References:

• Emails deleted from Outlook.com are reverting back to the Inbox
• Delete email in Outlook.com
• Deleted Skype contacts still appear in your Outlook.com contacts
• Use intelligent technology in Outlook on the web and Outlook.com
• Search Mail and People in Outlook.com
• Mail goes to the Junk folder by mistake
• I need to talk to someone!! - Microsoft Q&A
• Need to speak to a agent I am getting pop up draft scam emails - Microsoft Q&A
• How do I get a live person at Microsoft.? - Microsoft Q&A
• SPEAK TO LIVE AGENT - Microsoft Q&A