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Exchange 2013: breaks internal outlook anywhere when installing third party SSL

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Dear Forum,

My company recently purchased an SSL from a third party to properly configure outlook anywhere.

The request and registration went fine. However when assigning the proper services to the ssl certificate. this seems to break the internal ourlook-to-server connection from working.

I tested outlook anywhere and it worked fine.

Some additional info.

In the server setting of the Exchange 2013 I have the internal address (e.g)A: Server-Exchange.mydomain.com

External address(e.g)B: Exchange.contoso.com

When i looked into the a user setting I see that the outlook is configured to use outlook anywhere inside. 

My questions are: Is there a reason for using outlook anywhere inside( is this how exchange 2013 normally is configured)

Why does the enabling of the ssl change the internal setting for the outlook client fromA to B?


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