Outlook 2019 - Exchange 2016 On Premises - Non-Domain Login

Dave Krugler 21 Reputation points
2023-01-06T04:34:29.553+00:00

Just purchased a new laptop that I was not planning on joining to our domain for a remote employee. Purchased 2019 Office and tried to connect Outlook to our on-premises Exchange Server 2016. Anyway, entered his information to get outlook setup, and all it does it continuously ask for the password over and over and I cannot get past it. No error message, nothing in event viewer. Thinking it was the new laptop, I fired up a virtual machine with Window 11. Amazingly enough, same problem, continuous request for the password, regardless of the "remember" setting. Thinking it was Windows 11, fired up a virtual windows 10 machine, and same problem, endless password request. I had just rebuilt a win10 machine a month ago and had no problems logging in, so I joined the test win 10 to the domain, logged in and Outlook setup like a charm. Joined the Windows 11 machine to the domain, same, Outlook logged in.
Question is, what do I have to change on the exchange server to allow a non-domain computer to have outlook connect to it.
Microsoft Remote Connectivity Analyzer only complains about the ssl certificate (only 7 employee's, no need for the premium certificate). Exchange server is the latest from Nov 22 (15.1.2507.016), BPA only complains about TTL on the internal network. Remote internet or internal makes no difference.

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  1. Kael Yao-MSFT 37,646 Reputation points Microsoft Vendor
    2023-01-20T07:51:22.64+00:00

    Hi @Dave Krugler

    Thanks for the information.

    Glad to hear the issue has been resolved!

    While due to the forum policy, the question author cannot accept his own reply as the answer to the question.

    I have written a summary of this question so it can also help other community members.

    Please feel free to accept it as answer to highlight it.

    Thanks again for the sharing.

    [Outlook 2019 - Exchange 2016 On Premises - Non-Domain Login]

    Issue Symptom:

    Outlook 2019 installed on non-domain joined device cannot login mailbox hosted by Exchange 2016 server and keeps prompting for password.

    Resolution:

    Adding the DOMAIN.COM to the UPN suffixes, and then switching the user to Domain.com.

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  1. Dave Krugler 21 Reputation points
    2023-01-19T23:24:34.9+00:00

    To answer Kael's question, OWA is working, (Including Phone access) however, We were still pretty old school (as SBS 2003 shows) so I had not setup UPN suffixes yet, simply because I hadn't needed to up to this point. I used the info on this website....
    https://4sysops.com/archives/understand-the-upn-and-samaccountname-user-account-attributes/

    After adding the DOMAIN.COM to the UPN suffixes, and then switching the user to Domain.com, allowed me to log in properly.

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  2. Gopal Agarwal 406 Reputation points
    2023-01-20T04:27:28.1466667+00:00

    The issue may be related to authentication settings on your Exchange Server 2016. Specifically, it may be that the Exchange Server is configured to only allow domain-joined devices to connect to Outlook and is not allowing non-domain devices to connect. To allow non-domain devices to connect to Outlook, you can try the following steps:

    1. Open the Exchange Management Console and navigate to the Organization Configuration > Client Access.
    2. Under the Outlook Anywhere tab, ensure that the "Basic Authentication" option is checked.
    3. Restart the Microsoft Exchange Information Store service to apply the changes.

    You can also try to configure the exchange server to allow basic authentication.

    Alternatively, you can try to update your SSL certificate to premium one which will solve the issue with Remote Connectivity Analyzer.

    Please note that these are general steps, and the specific settings and options may vary depending on your particular Exchange Server configuration.

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