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Outlook 2010 http connection fails

Posted on 2011-09-02
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Last Modified: 2012-05-12
I have just installed a SBS2011.  
I also have applied a valid Thawte 123SSL certificate and have confirmed that this is working.

 I have 10 users which logs in to the domain from their laptops and access their email with locally installed Outlook 2010.
I use the autodiscover function in Outlook to set up their mail accounts.

BUT!!!
I also have 5 clients using laptops outside the LAN.
These 5 pc's does not log onto the domain nor is configured for this.
Outlook is therefore configured manually with exactly same settings as the other Outlook clients.
This includes settings under "more settings" "network" and "HTTP".

These clients was configured and tested inside the LAN and Outlook worked perfectly.
However when the clients goes outside LAN  Outlook fails to connect!

Any ideas?
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Question by:Ohmit
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Expert Comment

by:Cliff Galiher
ID: 36472095
Inside the LAN, machines (domain joined or not) will default to MAPI connections (even if HTTP is checked) and falls back to HTTP only if there is a problem. So, right now, there are several possibilities:

1) outlook anywhere on the server is not configured or failing.
2) you are not allowing inbound OA traffic at your firewall.

On a related note, SBS 2011 fully supports autodiscover, so manually configuring your non-domain machines should not be necessary. If autodiscover is failing, that is a further sign of a firewall issue.

Start with testexchangeconnectivity.com. That can help identify issues.

-Cliff
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Author Comment

by:Ohmit
ID: 36472403
Hi Cliff (my hero :-)  )

I can confirm that the test went ok but only when I entered the connect information.
The outodiscover function didn't work.

I can confirm though that when I configure computers logged in to the domain inside LAN the autodiscover works!
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Accepted Solution

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Cliff Galiher earned 500 total points
ID: 36472411
Okay. Let's tackle that. This shoukd get autodiscover working for you IF you are forwarding port 443 inbound on your firewall to SBS.

http://www.thirdtier.net/2009/02/setting-up-an-external-autodiscover-record-for-sbs-2008/

-Cliff
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Expert Comment

by:Cliff Galiher
ID: 36472415
FYI, while the article was written for SBS 2008, I can confirm that this works for 2011 as well.
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Author Comment

by:Ohmit
ID: 36473131
This is great :-)
Company is closed for the weekend so I won't know until monday :-)
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Author Comment

by:Ohmit
ID: 36485332
no news due to illness!
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