Autodiscover Externall does not work (Full Version)

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syntax1127 -> Autodiscover Externall does not work (28.Feb.2016 3:45:20 AM)

Hello all,

I am facing a really difficulties configuring autodiscover for my sbs2008 server, Unfortunately with no luck.

My purpose is to migrate my SBS2008 to office365 but in order to do that I would like to use the Cutover migration tool and in order to use that I have to make sure that my external autodiscover service is working perfectly.

I would like to accomplish a situation where my users will be able to configure outlook from outside the domain and from every computer.

Here is what I have configured:

1. I do have an UUC/SAN trusted certificate from godaddy with the following domains:
2. I have configured the public(External) DNS Records to look like this:

A record - -- points to my external public wan IP address

MX record - Points to my mail really server

and according to this post:

I have configured SRV Record with autodiscover to point to ( Should I point it to )

3. My SBS2008 server is configured with mydomain.local and not so I think this is the cause of my problem.

When I try to connect an external Outlook client I get a pop up from outlook with an error messaged say: The connection to Microsoft exchange is unavailable. Outlook must be online or connected to complete this action.

And then when I press OK, I get the authentication pop up with my internal server name: servername.mylocaldomain and on the mailbox window I get ( Screenshot is attached )

It seems that I do get to my server from outside ( No firewall issues ) but the authentication or the access to the mailbox is fail from some reason .

Here are some more details and steps I have taken:

I have added a UPN suffix to my domain so it will recognize (Using Active Directory Site and Trusts). I have also changed the users to match according to this s post:

I have added new DNS zone in my SBS2008 in order to make the external domain be recognized. I have added A records as well.
Changed the Outlook anywhere authentication from basic to NTLM.
Reboot the SBS server.
What am I misiing? No matter what I do the autodiscover service does not work :-(

I really need to make it work. Please help.

Thanks in advance.

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