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SSL/MSSTD settings Outlook anywhere

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All,

just want to raise a question, as I noticed a strange behaviour.

I have Exchange 2013 with Outlook Anywhare configured in this way:

So external and internal hostname is the same, SSL required only from external.

Internal connection works just fine and Outlook doesn't set the flag and the MSSTD setting for SSL.

Externally, If I setup from scratch, it's working as well, and the msstd is flagged and setup.

Problems begin when I migrate mailboxes from an Exchange 2010 in coexistance, which will be decomissioned in the future. After migration, user's Outlook (connected from external AND not domain-joined) was properly reconfigured BUT for the msstd setting which was missing.

As result the Outlook connection was totally flickering, up and down every now and then plus keep "connecting" for the directory service.

Setting up the msstd setting manually, everything is fine.

Now, we know that in EX2013 the Autodiscovery behaviour has changed: http://support.microsoft.com/kb/2754898/en-us

Practically, it will try always the internal first host name first, regardless where you're connecting from.

I was wondering if: since the hostname is the same for both internal and external, would this lead autodiscovery in misinterpret the configuration (InternalClientRequireSSL is set to $False) and left the configuration unflagged in Outlook? And, if so, why on migrated mailboxes only ?

Any suggestion, answer and comment will be hughly appreciated!

Thanks!


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