Outlook won't stay connected to server. Shows Trying To Connect or Disconnected.

I have a strange problem. I had to reset my Yahoo account in Outlook Classic (I have done this frequently in the past). I created a profile for this mail account, and followed the instructions, getting a special password from Yahoo, specifying all the settings for servers etc. The process showed me that I was able to receive mail from the server and send mail through the server. Then I restarted Outlook (Classic), I saw the basic information created with my profile (such as Folder structure) , but the system would not download any messages, and it gave me an error saying that the connection with served could not be established. The strangest thing is that if I switch over to the NEW version of Outlook, everything seems to work well. Messages are downloaded . the file structure is created, etc. I tried creating other profiles, and the behavior is the same for any profile I try to connect to a Yahoo account

Hi @Gail Huss, 

Welcome to Microsoft Q&A Forum. 

Thank you for contacting us, and I’m sorry for the inconvenience you’ve been experiencing with Classic Outlook on Windows 11. 

From what you’ve shared, this often happens when credentials for that account are stuck or invalid. Your Gmail and Bellsouth accounts continue to work in the same Outlook profile, which confirms that Outlook is online and capable of syncing it’s just the primary Outlook/Exchange account that can’t connect.  

Here are my recommendations that you may find helpful:  

1/ Run the Outlook Connectivity Troubleshooter (Get Help) 
On Windows 11, open the Get Help app and search for “Outlook disconnect” or launch directly via this link: Start the troubleshooter.  

You can refer to this Microsoft article: Fix your Outlook email connection by repairing your profile - Microsoft Support 

2/Create a fresh Outlook profile 
Open Control Panel → Mail → Show Profiles → Add, then re-add your account. After testing, set the new profile as default if the issue is resolved. Create an Outlook profile - Microsoft Support 

3/ Clear any stuck credentials 

• Open Credential Manager → Windows Credentials and remove entries related to Outlook/Office/Microsoft 365 (e.g., MSOffice, ADAL, your work account).  
• Sign in again when prompted. 
• 

4/ Reconnect your work/school account in Windows 
Settings → Accounts → Access work or school → Disconnect, then Connect and sign in again with your Microsoft 365 account. 

5/ Use Outlook on the web or New Outlook temporarily 
If email continuity is critical, sign in at outlook.office.com or try New Outlook while we stabilize Classic Outlook.  

6/ Online Repair (last resort) 

• Settings → Apps → Installed Apps → Microsoft Office (or Outlook) → Advanced Options → Repair or Reset. 
• 

7/ Contact Microsoft Support  

If the issue persists even after these steps, it may stem from a deeper system-level cause. In this case, I recommend contacting your company's IT administrator, who can submit a support request to Microsoft through the Microsoft 365 Admin Center. They’ll be able to access system-level information to investigate the issue thoroughly and provide assistance. At the very least, they can offer the most effective workaround to ensure your experience remains smooth and secure.     

We kindly ask for your understanding that, as moderators, we do not have access to the administrative tools or permissions required to investigate or modify these configurations. We also do not have the capability to initiate remote sessions for direct assistance. Our role is to guide users to the appropriate resources and support channels.    

I hope the information provided proves useful. Please proceed with the outlined steps and let me know whether they resolve the issue. If not, I’ll be glad to continue working with you to find a solution.   

If you find my post helpful, kindly consider marking it as the accepted answer. Doing so can assist others in the community who may have similar questions in finding solutions more quickly.     
Thank you for your kindness and contributions to the forum.    

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If Outlook is showing a status of "Disconnected" or "Trying to Connect," there are several steps you can take to troubleshoot the issue:

1. Check Network Connection: Ensure that your internet connection is stable. Since your Gmail and Bellsouth emails are working fine, the issue may be specific to Outlook.
2. Disable IPv6: If you have IPv6 enabled on your network adapter, it may cause connectivity issues with Outlook. You can disable it by going to Control Panel > Network and Sharing Center > Local Area Connection > Properties, and then unchecking Internet Protocol Version 6 (TCP/IPv6).
3. Run Windows Update: Make sure that your Outlook client and Windows operating system are up to date. Outdated software can lead to connectivity problems.
4. Check for Service Issues: If multiple users in your organization are experiencing similar issues, check the Microsoft 365 Service health status to see if there are any ongoing problems with Exchange Online.
5. Repair Outlook Profile: Sometimes, a corrupted Outlook profile can cause connectivity issues. You can create a new profile to see if that resolves the problem.
6. Use the Microsoft Support and Recovery Assistant: This tool can help diagnose and fix various Outlook connectivity issues automatically.

If these steps do not resolve the issue, it may be beneficial to reach out to Microsoft support for further assistance.

References:

• Fix Outlook connection problems for Microsoft 365 account
• Outlook displays a Disconnected status when IPv6 is enabled