Exchange 2010 and outlook anywhere

Hello everyone,

I'm hoping that someone can help me on this.  I've separated this question out from my previous one because first of all my IP address was in there and second of all the response that was made to it pointed me in a brand new direction.  For some reason, I'm unable to get Outlook Anywhere working with our Outlook 2010 clients, but it works fine with Outlook 2013 and Outlook 2016 clients.  I've run into a bit of a brick wall here trying to troubleshoot this issue.  The system can configure the mail just fine, but for some reason it can't log into the server.  However, running the Microsoft Connectivity Analyzer works (I've attached the report).  Both Outlook Anywhere and Outlook Autodiscover work, but Outlook 2010 clients can't connect, or "Log In" to the server.  When the outlook profile is set up, it gets all the way to the last step and then gives the message "The connection to the Microsoft Exchange is unavailable.  Outlook must be online or connected to complete this action."  Once you launch outlook it just says "Disconnected" -- no password prompt or any other thing indicating that it's confused, it's just disconnected.  We run Exchange 2010 on the back end and the laptops work fine if connected to the VPN, there is something evading us and I don't know what it is.  

So, what I've done to troubleshoot this problem is:
  • Set up Outlook locally and try and run it remotely
  • Attempted to set up outlook remotely
  • Run the connectivity analyzer and had it pass
  • Connected to the VPN when remote and the e-mail works
  • Tested the e-mail locally and it works
  • Tested remote connectivity with Outlook 2013 and Outlook 2016 and it works

Any help with this would be greatly appreciated.

Sincerely,

Steve
RCATestResult_2016-09-08.html
Steve AlmesIT ContractorAsked:
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FOXActive Directory/Exchange EngineerCommented:
On one of those workstations with outlook 2010 see if you can connect via Outlook web access from a browser.  If not post the error.
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Steve AlmesIT ContractorAuthor Commented:
Yes, I forgot to mention that, I can connect fine from that workstation to OWA.

Thanks,

Steve
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FOXActive Directory/Exchange EngineerCommented:
Being that you said your outlook 2013 clients are connecting correctly I want you to check the security settings on one of those workstations and compare them to a 2010 client.

On an outlook 2013 client File> Account Settings>Account Settings>double-click the email account>more settings>Security tab(view those settings
Also view the settings in Connection

ref link to troubleshoot outlook anywhere connectivity issues:
http://searchexchange.techtarget.com/tip/Troubleshooting-Outlook-Anywhere-Where-to-start
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Steve AlmesIT ContractorAuthor Commented:
One of the major problems that I am having is that the settings are not immediately visible on Outlook 2016 now that everyone has upgraded.  The connection tab and security tab for Outlook 2016 are not there any more, they have "simplified" (read; dumbed down) the configuration on the new Outlook 2016 so it's pretty much impossible to compare settings between the two.

Thanks again,

Steve
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Steve AlmesIT ContractorAuthor Commented:
I ended up calling Microsoft and they found that there was an issue with a DNS record that was used internally that was resolving outside the network.  Once that record was removed, everything started working.  No answers here, though... thanks for trying.
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Steve AlmesIT ContractorAuthor Commented:
Solved by myself and Microsoft
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