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timroland-4740 asked ZhengqiLou-MSFT commented

Outlook 2016 Won't Log onto Exchange 2016

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?

office-exchange-server-connectivity
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timroland-4740 answered ZhengqiLou-MSFT commented

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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Hi @timroland-4740 ,

Where do you installed the Outlook client? The Win10 computer? If so please check the ports between the Exchange server and this computer.
Can you try another version Outlook?

Please also try Test-email configuration (CTRL + Outlook icon), use autodiscover to test, and recycle the AutodiscoverAppPool, MAPIPool.
If you have set the DNS records, you could test it with https://testconnectivity.microsoft.com/tests/Ola/input

Best regards,
Lou


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Hi @timroland-4740 ,

Do the suggestions above help? If the issue has been resolved, please click “Accept as answer” to mark the helpful reply as an answer, this will make answer searching in the forum easier and be beneficial to other community members as well.

If you are still stuck in this issue, please feel free to post your questions.

Regards,
Lou


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timroland-4740 answered ZhengqiLou-MSFT commented

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.

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Hi @timroland-4740 ,

How is everything going? Does this issue resolved?
After researching, I found an article that says the backend should use the default self-signed Microsoft Exchange certificate, not the third-party one. I've edited the above answer and here is the article: https://docs.microsoft.com/zh-cn/archive/blogs/miguelo/exchange-2013-clients-not-able-to-connect-using-outlook-anywhere

Sorry for my mistake.

If the issue is still there, please feel free to post anything you want to know.

Best regards,
Lou

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ZhengqiLou-MSFT answered ZhengqiLou-MSFT edited

Hi @timroland-4740 ,

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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