Outlook 2016 is not connecting to Exchange Server 2010 on an iMAC?

Outlook 2016 is not able to successfully communicate with Exchange server 2010 in a local network environment.
Emails are not being retrieved, even though it is online.
Any suggestions?  We are using the local domain name.
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IvanSystem EngineerCommented:

Outlook on MAC can create alot more connections then Outlook on Windows. I had this problem, but not with 2016 (still didnt try it). Users were complaning that email is received with hour delay or something like that.
Anyway, solution was to create new throttling policy and apply to mailbox of users that have mac computers.

It goes like:
New-ThrottlingPolicy -Name Apple
Set-ThrottlingPolicy -identity Apple -EwsMaxConcurrency 20
Set-Mailbox -identity "username" -ThrottlingPolicy Apple

I would investigate a bit more, before applying this policy. Check logs, browse a bit more..
or simple create new policy and apply to one user..and check.
You can always remove it.

100questionsAuthor Commented:
Thanks. Will take a look.  Problem is that when setting up the email and trying to connect to the email - a certificate that we don't want is showing up - and I don't want to connect to it.  Not sure where it's getting the certificate from but it's wrong..
IvanSystem EngineerCommented:
Oh, so there is a certificate problem as well.
What pop up do you receive? Is this only on Outlook 2016 on iMAC or with other versions of outlook and windows clients?
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100questionsAuthor Commented:
Outlook 2016 only actually, just installed it.
I tried flushing the DNS, unbinding the iMAC from the domain, and still I am getting this issue.
Pop up is similar to this..

Verify Certificate
A secure connection cannot be established with the server.... because it's intermediate or root certificate cannot be found.  Do you want to continue?

Then it shows the details on the certificate and I have the option to trust or never trust etc..
100questionsAuthor Commented:
Even when remotely signed in using wireless, trying to connect to the Exchange Account, I am seeing that same certificate request.
100questionsAuthor Commented:
@spriggan13 - issue is that the connection shows orange not green and there is a certificate issue.
IvanSystem EngineerCommented:

and from where did you publish certificate from Exchange. From internal CA or from 3rd party CA?
Sometime when receiving certificate from trusted 3rd party CA, you get intermediate cert.
If that is the case, maybe you should try to import it into mac?
Or if it is from internal CA, then maybe you need to import it as well.

Something in that line of action...
100questionsAuthor Commented:
This is not a certificate i want to trust however, since the server on site should be offering it's own certificate..
100questionsAuthor Commented:
Would importing an olm from a saved Outlook 2011 account help?
100questionsAuthor Commented:
The problem is that Outlook for MAC 2016 will work with Exchane 2010 SP2.

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100questionsAuthor Commented:
This is the requirement, othee issues are secondary.
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