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Exchange 2013 OutlookAnywhere/AutoDiscovery/Outlook2013 client issues outside company network

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Hello,


I have a single Exchange 2013 server with some clients outside the company network/domain. I am having problems with a non-domain computer with Windows 8.1 Outlook 2013 (with latest updates installed both client & server). 

I have configured Outlook Anywhere & Autodiscovery and it works fine according to the results from ExRCA. Both autodiscovery & outlook anywhere. I have a valid certificate (not a wild cert), specifically for the mail server.  Autodiscover addresses are in the certificate too. 

When trying to set up a connection outside network on a non-domain computer, I get past the account settings, all green checkmarks but when it's trying to establish a connection, it waits for a certain period of time and throws this error:

"the connection to microsoft exchange is unavailable. outlook must be online or connected to complete this action"

I really don't understand what the problem might be. Any help/direction would be appreciated. 


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