Autodiscover for Outlook is not functioning properly on macOS

Hello, @ahmed ali,

Welcome to the Microsoft Q&A platform!

Based on your description, when you use Outlook on macOS, Outlook frequently displays a “Disconnected” status, and the problem remains unresolved even after trying multiple workarounds.

Here are some steps to resolve Autodiscover and connectivity issues with Exchange On-Premises 2019:

1.Check Autodiscover Configuration: Verify that your Autodiscover service is correctly configured and accessible. You can test this using the Microsoft Remote Connectivity Analyzer tool.

2.Check DNS Settings: Ensure that your DNS settings are correctly configured for Autodiscover. The DNS records should point to the correct Autodiscover service.

3.Exclude HTTPS Root Domain: The Autodiscover process sometimes receives unexpected results from a third-party web server. You can create an Outlook registry key to exclude the HTTPS root domain. This is a temporary workaround, and you should remove the registry key once the issue is resolved.

4.Use Outlook on the Web: As a temporary solution, you can use Outlook on the Web (formerly known as Outlook Web App) to access your email while troubleshooting the issue.

5.Network and Firewall Settings: Verify that there are no network or firewall settings blocking the Autodiscover service or IMAP connections.

6.Check SSL Certificates: Make sure your SSL certificates are correctly installed and not expired. The clients might be failing due to certificate issues.

7.Check Exchange Settings: Ensure that your Exchange server is properly configured for client access, including Autodiscover, EWS (Exchange Web Services), and MAPI over HTTP.

8.Client Log Files: On the Mac client, check the log files for any specific errors: In Outlook, go to “Preferences” -> “Accounts” -> Click on the account -> “Advanced” -> “Server” to ensure that all server settings are correct.

Moreover, here are some documents which may be helpful to you:

1.https://zcusa.951200.xyz/en-us/exchange/troubleshoot/outlook-issues/issues-when-using-autodiscover-service#workaround.

2.https://support.microsoft.com/en-us/topic/outlook-for-mac-clients-cannot-connect-to-exchange-server-bb7690e0-975a-7d95-a29b-b8bf5e787cb3.

If these steps do not resolve the issue, you might need to enable detailed logging on the Exchange server and on the client side to capture more information about the issue for further troubleshooting.

At the same time, Microsoft has a dedicated support team for Outlook for Mac. It is suggested that you directly contact this support team by clicking Contact Support in the Help menu in Outlook for Mac. That team will assist you further.

Should you need more help on this, you can feel free to post back. 

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Thank you for your support and understanding.

Best Wishes,

Alex Zhang