Unable to Setup Outlook Account Through Exchange Server

Normally, when I setup an email account for a staff member, it is a straightforward process, especially for that first email account.

Outlook starts up, asks me if I want to create an account, to which I reply yes.  I enter the name, email address, and password, and normally, the computer connects to the Exchange email server, and Lo!... I get an account setup and all mail for the user copied to a new OST file.

But, all of a sudden, this isn't working at all.  Upon trying to connect to the server, I get the error message, "An encrypted connection to your mail server is not available.  Click Next to attempt using an unencrypted connection".  Naturally, that doesn't work, either.

There is no question that I have the correct domain name, correctly spelled, as well as the user's correct email address.  What can be happening?

TIA

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Wayne HerbertIT SpecialistAsked:
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Wayne HerbertIT SpecialistAuthor Commented:
Test connectivity failed... clearly something changed with Intermedia Exchange server.
 
I found this KB article:  https://kb.intermedia.net/article/1306

I added the autodiscover subdomain, then added the CNAME record and now Outlook now connects to the Exchange server and auto configures.

Why things changed is unknown to me... I've been setting up email accounts with Intermedia Exchange for more than 2 years before this issue popped up.
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Wayne HerbertIT SpecialistAuthor Commented:
I should add that this is a hosted Exchange account, handled by Intermedia.
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IvanSystem EngineerCommented:
Hi,

I would run Microsoft Remote Connectivity Analyzer https://testconnectivity.microsoft.com/ for that user, both Outlook tests (Connectivity and Autodiscover).

If everything is ok, then you can look for Outlook/ computer/ something else as a problem.

What Outlook is this, 2016? If so, do you have more users with this type of Outlook?

Regards,
Ivan.
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Wayne HerbertIT SpecialistAuthor Commented:
I have previously had the user on Outlook 2016 without issue.  However, lightening zapped her PC and I need to put her on a spare with Outlook 2013 while I rebuild the faulty PC.  Was supposed to be easy peasy.  Will try the connectivity bit.  Thank you.
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IvanSystem EngineerCommented:
Oh, well.. good thing is that the problem is solved :)

Regards,
Ivan.
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Wayne HerbertIT SpecialistAuthor Commented:
I accepted my own solution because a Google search revealed an Intermedia KB article which described steps for Outlook auto connect.  What it did not describe is why things changed on me but it did solve the problem.
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