SBS 2011 Exchange Activesync - Outlook won't connect but iPhone does

Posted on 2013-06-11
Medium Priority
Last Modified: 2013-06-12
Hey Guys

I hope someone can point me in the right direction.

I have an SBS 2011 server and I have enabled Exchange Activesync for Outlook Anywhere and iPhone sync.

I setup the Activesync on the iPhone and that's working normally.

However, in Outlook I just get the following error  "The action cannot be completed.  The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action"

What do you think I'm doing wrong with the configuration?
Do you think it's a client config issue or have I missed a setting on the server?

Kind Regards
Question by:moncomp
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LVL 41

Expert Comment

by:Philip Elder
ID: 39239980

Small Business Server 2011 Standard (SBS) is set up using the Getting Started Tasks based wizards found in the SBS Console.

There is no need to manually configure pretty much anything on SBS after running those wizards.

In fact, manually changing things can actually _break_ things in an SBS deploy.

We have an excellent SBS STD setup guide here: http://bit.ly/p3YbXO

Please re-run Connect to the Internet and the Internet Address wizards to get that part up. If using a third party certificate then run that wizard to reseat the existing certificate choosing that option.

You can then run the Fix My Network wizard to work out any further bugs.


Author Comment

ID: 39240899
Hey Philip

Thanks for the SBS STD setup guide. Really helpful:)

I haven't changed any of the default settings for Activesync. So I wonder what could be going on. I am also using self signed certificates.
I can re-run "Connect to the Internet and the Internet Address wizards". Do you think I need to? Don't you think it's strange that the iPhone will connect but Outlook won't (keep in mind any laptop that is connected locally to the domain Outlook works. Outlook just won't work externally to the network on any laptop with any user)?

Have I got a firewall setting wrong perhaps? Or do you think it's definitely something on my SBS server causing the issue?


Author Comment

ID: 39240935
The only other thing I can think of is that maybe I'm entering the wrong information in Outlook when I setup the account
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Author Comment

ID: 39241086
hey Philip

I ran the Exchange connectivity analyzer from: https://www.testexchangeconnectivity.com/
I tested RPC/HTTP connectivity.

I get a failure on the SSL certificate. Here are the failure results:

Testing the SSL certificate to make sure it's valid.
       The SSL certificate failed one or more certificate validation checks.

Certificate trust is being validated.
       Certificate trust validation failed.
      Test Steps
      The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=remote.****.com.
       A certificate chain couldn't be constructed for the certificate.
      Additional Details
       The certificate chain couldn't be built. You may be missing required intermediate certificates.

I'm wondering if I am missing a certificate or if I need to rebuild one.
What do you think?

Author Comment

ID: 39241197
Definitely not a firewall issue. Port 443 is visible from the the internet to the server.
LVL 41

Accepted Solution

Philip Elder earned 2000 total points
ID: 39241479
Is the certificate self-issued or third party?

Self-issued requires an install on the remote machine. Third party does not.


Author Comment

ID: 39243289
Hey P.

You were right! I had previously imported the certificate but when I checked it was gone.
I grabbed the certificate installer from \\server\public\downloads share\   and installed it.
Now working normally! :)

Thanks for your help guys. Can't believe I missed something so basic :-}

Kind Regards
LVL 41

Expert Comment

by:Philip Elder
ID: 39243307
A GoDaddy certificate can be found for $13 per year. There is really no reason in this day and age to be using self-issued certificates anymore.

Glad to help.


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