Microsoft Outlook trying to connect

Question

Microsoft office has been "trying to connect" all day. I usually use Classic but I tried switching to new. New informs me that I have a cryptographic exception and troubleshooting found no solution for the problem. The latest version of Microsoft 365 and Office are installed on my computer. I can connect to the internet and other 365 products like Excel work correctly. I've tried making all of my Outlook Add-ins Inactive. I went to Account Settings, selected my account but the option to Repair my account is greyed out.

How can I resolve this issue?

Answer 1

Hi @Elizabeth L

I understand how frustrating it is that the new profile also cannot connect.

Since the new profile returns “an encrypted connection to your mail server is not available,” this may be related to how Outlook is discovering the account or reaching the mail server, rather than the original profile.

Please try the following:

• Temporarily disconnect any VPN or proxy and test Outlook on another network, such as a mobile hotspot.
• Open the Windows Get Help app, search for Set up Microsoft 365 email in Outlook, and run the Classic Outlook Profile Setup troubleshooter.
• Confirm whether the affected address is an Outlook.com/Hotmail account, a Microsoft 365 work or school account, or an account from another email provider.
• If it is a third-party account, verify the current IMAP/SMTP settings and whether an app password is required with the email provider. Please do not continue with an unencrypted connection.
• If it is a Microsoft 365 account using a custom domain, the domain administrator or hosting provider may need to verify the Autodiscover configuration.

Also, please check whether you can send and receive messages normally through the account’s webmail. This will help determine whether the connection problem is specific to the Outlook desktop application on this computer.

Please feel free to let me know if you have any further updates, thanks.

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