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Outlook Anywhere to SBS 2011

Posted on 2014-11-17
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Last Modified: 2014-11-21
I am trying to set you Outlook Anywhere on a SBS 2011 box. It looks simple. Enable OutlookAnywhere and done. The keep referring to forwarding SSL/HTTPS through the firewall. Is that the same as just normal HTTPS?

OWA works fine. I just can't get Outlook Anywhere to work. Am I missing the SSL\HTTPS port through the firewall? The remote Outlook client just won't find the server.....
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Question by:LockDown32
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by:Cliff Galiher
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OA is ready to go on SBS 2011 out of the box. OA and OWA both use 443, so if one works, so should the other. The usual cause for OA not working is external DNS issues not related to SBS.
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by:LockDown32
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OK. That is what I thought but the DNS entry is the same for both OWA and OA isn't it? mail.domain.com?

Do you mean DNS issues on the client side?
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by:David Atkin
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Can you upload a screenshot of your setting please?  Black out the domain if you're not comfortable with us knowing.

Presuming you're using the local server name when specifying the exchange server and adding the OWA address in the remote section?
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by:Cliff Galiher
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If the client is external, then it'd need to use an external DNS server to look up the OA server name you provide. So yes, I am talking about client and external DNS records. Also, don't confuse OA and autodiscover. They are often used in tandem, but are different services and each has their own DNS requirements. One can be misconfigured while the other is working fine.
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by:LockDown32
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I don't use Autodiscover. I just tried Microsoft's Remote Connectivity Analyzer for OA (without the auto discover) and it passed. Does that mean the problem is in my outlook?
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by:LockDown32
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Sorry David. What settings would you like a screen shot of? Server or client?
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by:David Atkin
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If you can show us the account settings of the outlook client that would help.

Control Panel > Mail > Email Accounts

Double click on the account and take a screenshot of these settings and the More Settings section where you specify the outlook anywhere settings.
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by:LockDown32
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I have no problem with giving the domain. It is gsmetalinc.com

I just added a user to test. It is TestUser and the password is the same TestUser. Can someone verify that the Remote Connectivity Analyzer does pass the OA test to make sure I'm not on drugs?
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by:LockDown32
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Screen shot attached
Capture.PNG
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by:Cliff Galiher
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I noticed you have the authentication method set to NTLM. I am not in a position to spin up my SBS 2011 lab VM, but as I recall, the default config for OA in SBS is to use basic. Over HTTPS, there is not really a security benefit to NTLM, and NTLM doesn't always work well with some NAT implementations, hence the decision to make basic the default.

It is also possible that you did change to NTLM on the server end, but then we are still back to NTLM being less predictable over some NAT implementations, so you may simply be seeing the result of that. I'd recommend trying basic on both the client, and if you changed it on the server, changing it back...they need to match, obviously.
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by:David Atkin
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Hello,

Tick the option for 'Only Connect to Proxy servers that have this principle name in their certificate'
Enter the value:  'msstd:mail.gsmetalinc.com'

Change the Authentication to BASIC.

Is the client on the domain?  If not, do you have the certificate installed? (If self signed)
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by:LockDown32
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So far none of the above options seem to work. NTLM is the default on both the server side and the client side but I did try basic. No joy.

OWA works (https://mail.gsmetalinc.com/OWA) with the test user and the certificate looks fine. Microsoft's Connectivity Analyzer has one small warning but it passes.

'msstd:mail.gsmetalinc.com' didn't do anything different

I am running out of ideas :)
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by:David Atkin
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Does the client work locally?
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by:LockDown32
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I am trying to find a local workstation that has Office 2010. I will let you know.....
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by:LockDown32
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I did find a local copy of Outlook 2010. It worked great except for the SSL Cert but it found and took the server and user. I have read a couple posts where people had to open other ports in addition to 443. Any ideas?
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by:David Atkin
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Port 443 is all you should need.

What error did the analyser show?

Presuming you're putting the local server name when specifying the exchange server (before the advanced settings)?
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by:LockDown32
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Attached are the screen shots of the Analyzer and the error. I am a little lost on your reference "Presuming you're putting the local server name when specifying the exchange server (before the advanced settings)".
 
   I don't see Advanced Settings in the analyzer.
Capture1.PNG
Capture2.PNG
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by:LockDown32
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BTW if you want to play with the Analyzer the password for TestUser is TestUser
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David Atkin earned 500 total points
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Sorry when I said specifying the exchange server I meant when setting up the email client.

See attached.

Also, I wouldn't advise advertising any login details on here.  Although I have no reason to doubt any of the other experts, you never know what peoples intent may be.
TestUser.PNG
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by:LockDown32
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Thanks David. That was the problem. I was not using the local server name.
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by:David Atkin
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Great, glad you got it resolved.
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