Outlook 2016: Autodiscovery not working (Office 365/Germany Cloud)

We originally encountered this problem during the configuration of Office 365 Germany, but since the root cause of the problem is unknown, this workaround might also resolve issues with “regular” Office 365. The issue affects Outlook 2016 and previous versions as well as Outlook for Mac.

Problem

When you try to set up a new mail account for Office 365, you receive an error message and the profile is not set up. This error occurs whether you use the “Add new account” wizard in Outlook or the “Add new profile” wizard in the control panel.

The following error message is displayed:
“An encrypted connection to your mail services is not available.”

Trying to set up an unencrypted connection will fail as well.

Since you can’t configure the server settings manually, this error prevents you from using Outlook 2016 unless you are able to resolve the issue.

Cause

The cause of this error is currently unknown (to us).

Known autodiscovery Issues

Unrelated to the issue resolved in this post, there are several other reasons autodiscovery might not work:

  • A spelling error in the email address
  • The domain or the DNS records are not set up properly, especially the autodiscovery CNAME
    • An old DNS record points to the wrong Server (either client DNS cache or company DNS Server)
  • The required updates for Outlook are not installed
  • If Active Directory synchronization is used, the user in the local Active Directory might incorrect

You can gain additional information on why autodiscovery might not be working with this official tool: https://testconnectivity.microsoft.com/

Microsoft Support article regarding known issues

Solution

Creating an empty profile

The issue can be resolved by creating an empty profile instead of setting up the profile immediately.

  1. Close the Outlook application
  2. Open the control panel (view should be either small or big icons), then open “Mail (Microsoft Outlook 2016)”

3. Choose “Show profiles” to show a list of the existing Outlook profiles

4. Left click on “Add” to create a new profile

5. Choose a name for the new profile

6. Cancel the account setup wizard

7. Confirm the creation of an empty profile

8. Set the empty profile as default

9. Open the Outlook 2016 application and enter the email address

10. You will be asked for the credentials, unless they are already saved in the credential manager

11. After entering the credentials, you will be informed that the mail delivery location has been changed

12. You should now be informed that the account setup is complete