Outlook 2016 Won't Log onto Exchange 2016

tim roland 6 Reputation points
2021-07-20T19:05:35.903+00:00

Isolated switch, fresh installs of Exchange 2016 (no whammies), new DC and new Win10 WS all in a virtual environment. They can all see one another fine.

Certificate Authority and DNS on DC and certificate issued to Exchange server. Other than one new user there are literally no other changes implemented.

No apparent issues with Exchange connectivity as ECP connection is fine. Can access Exchange using workstation and OWA with no issues. Test email to same user goes and comes back.

When flashing up Outlook 2016 it picks up user details but then chokes on "Logging on to the mail server".

Googled the heck out of it and tried everything and rebuilt fresh for a clean slate. Same issues.

It can't be much. Any fresh ideas?

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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  1. tim roland 6 Reputation points
    2021-07-21T12:21:21.733+00:00

    Wow! I so much appreciate the time and effort you put into trying to help me out.

    Everything is as above accept the certificate wasn't bound to the Exchange Back End so I had a little moment of exhilaration followed by a let down ha ha.

    Ran the test and received a "succeeded" response.

    When I run Outlook on the workstation it picks up the name and email and then just fails to log on.

    Hmmmmm......

    Once again, thank you so much for the well crafted response.

    1 person found this answer helpful.

  2. Xzsssss 8,871 Reputation points Microsoft Vendor
    2021-07-21T07:11:18.48+00:00

    Hi @tim roland ,

    After you applied the new Domain CA certificate, have you assigned IIS and SMTP service on it like this:
    116508-image.png

    If so, you should check if this certificate is used on IIS bindings, only on FrontEnd.
    And please use the following command to test the outlook connectivity:

    Test-OutlookConnectivity -ProbeIdentity OutlookMapiHttp.Protocol\OutlookMapiHttpSelfTestProbe | FL  
    

    In addition, have you add the cert to your Trusted Root Certification Authorities? If not, I think when you want to login to OWA or Outlook, there should be a certificate warning pop-up.

    Best regards,
    Lou


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  3. tim roland 6 Reputation points
    2021-07-21T16:52:24.303+00:00

    Holding CTRL and right-clicking the Outlook icon and looking at "Connection" brings up an empty window. All seems good but no connection. OWA and Exchange fine (or so it seems).


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