Cannot add account to outlook-problem connecting to server" "an encrypted connection to your mail server is not available"

Question

Hello

I hope someone can please help me.

On Monday I was unable to receive any new emails in my outlook app. It states it was disconnected from the server on sunday ( I had not used the laptop since friday and it was working perfectly then).

I am still able to access outlook online and access all other office apps.

I have tried various things to fix it ( repair, check for updates on office). One of the suggestions was to remove the profile and add the profile back in.

I have gone to control panel> Mail and tried adding an account.

I add in the new profile name and my details. When I get to the configuring stage, it establishes the network connection successfully but when it searches for my email settings it states " problem connecting to server" "an encrypted connection to your mail server is not available"

I dont want to continue with unencrypted but even when I do it still does not work, it states " we're sorry we couldnt set up your account automatically". I dont want to set up the account myself.

Please can someone help on how to restore my account/profile on my outlook app. 

Thanks in advance

Lady in distress!

Answer 1

Hi Lisa Jones,

Thank you for posting your question in the Microsoft Q&A forum.

Based on the error message you're receiving ("an encrypted connection to your mail server is not available"), it appears that Outlook is having difficulty using the Autodiscover service to automatically locate your mailbox server settings.

To help troubleshoot this further, I'd like to confirm a few details:

1. Is your email account hosted on Exchange Online (Microsoft 365) or an on-premises Exchange Server? Since you mentioned you can access Outlook Web App successfully, I suspect it's Exchange Online, but confirming this will help narrow down the cause.
2. Please run the Microsoft Remote Connectivity Analyzer test:
   • Visit: https://testconnectivity.microsoft.com/tests/O365Ola/input
   • Select "Outlook connectivity" test
   • Run the test and review the results

This tool will test the same Autodiscover process that Outlook uses and will provide detailed diagnostics about where the connection is failing (DNS, SSL certificates, authentication, etc.).

If the test succeeds but Outlook still fails to connect, the issue is likely on your local machine:

• Firewall or Antivirus interference: Security software may be blocking Outlook from connecting. Try temporarily disabling your antivirus/firewall to test.
• Proxy settings: Check if there are any proxy configurations that might be blocking the connection.
• Outdated Outlook: Ensure your Office/Outlook installation is fully updated via Windows Update or Office Update.

If the test fails, the results will indicate exactly which step is failing, please share the results of the connectivity test and I'll help you troubleshoot this issue further.

Reference: How to Fix "Outlook Encrypted Connection Is Not Available"

Note: Microsoft is providing this information as a convenience to you. These sites are not controlled by Microsoft, and Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please ensure that you fully understand the risks before using any suggestions from the above link.

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Answer 2

It seems you are encountering an issue with setting up your Outlook account due to the error message stating that "an encrypted connection to your mail server is not available." This typically occurs when Outlook is unable to connect to the mail server using the required encryption settings.

Here are some steps you can take to resolve this issue:

1. Check Your Email Address and Password: Ensure that you are entering the correct email address and password during the setup process.
2. Use Outlook Web App: Since you can access your emails online, consider using the Outlook Web App as a temporary solution while troubleshooting the desktop application.
3. Set Up a POP3 Connection: If you are unable to connect via Exchange, you might want to set up your account using a Post Office Protocol (POP3) connection. This can be done by following the instructions in the Outlook help documentation.
4. Update Outlook: Make sure that your version of Outlook is up to date, as updates can resolve connectivity issues.
5. Check Autodiscover Settings: The Autodiscover service must be properly configured for your domain. If it is not set up correctly, Outlook may fail to connect automatically.
6. Network Connection: Ensure that your network connection is stable and that there are no firewall or antivirus settings blocking Outlook from connecting to the mail server.

If these steps do not resolve the issue, you may want to consider reaching out to your IT support or consulting the Microsoft Community for further assistance.

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References:

• Encrypted connection to your mail server is not available
• Outlook can't set up a new profile by using Exchange Autodiscover for an Exchange Online mailbox in Microsoft 365