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Exchange 2013 Outlook Anywhere failing on Win7 Outlook 2013 on workgroup computer

Posted on 2014-07-21
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Last Modified: 2014-08-16
Hi,
  I have an Exchange 2013 running on Server 2012 R2 and have a mixed environment with some computers on the domain (and autodiscover works perfectly) and some workgroup computers that use Outlook Anywhere.  I have 6-7 computers successfully using this (winxp, vista and 7 clients) and the customer recently purchased two new windows 7 clients that refuse to work.  We continually get the error that the exchange server is not reachable (sorry for paraphrasing I dont have the error in front of me).

  The local IP of exchange is 192.168.1.13 and I am able to ping it by IP and by hostname mail.domain.com.  nslookup returns the correct IP when performing a lookup on mail.domain.com.  https://mail.domain.com/OWA works perfectly fine on the same computers that refuse to connect with Outlook Anywhere.  So that also tests the creds we are using and confirms they are correct.

  I disabled the firewall and AV on the computers to rule that out.  I also ran the following cmdlt without error:

get-outlookanywhere | set-outlookanywhere -internalhostname mail.domain.com -externalhostname mail.domain.com -internalcientsrequiressl $true -externalclientsrequiressl $true -defaultauthenticationmethod ntlm

  I have valid DNS entries for both the local zone and external zone including the autodiscover.  I am using a real UC SSL cert not self signed and the cert matches the names we are using.

  I am at a loss of what else to check or how to get more diagnostic info.  

Thanks in advance.
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Question by:compcreate
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Expert Comment

by:-MAS
ID: 40210644
You mean it is working internally or both not working?
Did you try with " On fast connections, Connect using HTTP first, then connect using TCP/CP" option ticked internally?
Try open outlook rpcdiag switch i.e ( type this command "outlook /rpcdiag")

Are you getting password prompt?
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Expert Comment

by:suriyaehnop
ID: 40210652
From that PC, are you to ping,nslookup for your autodiscover.

https://testconnectivity.microsoft.com/

Go to this link and install the Microsoft Connectivity Analyzer Tool and use it to test Outlook anywhere from this pc.
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Author Comment

by:compcreate
ID: 40211420
It is working both internally and externally for other computers of mixed OS and mixed outlook versions.  Two brand new win7 with outlook 2013 fail to connect.  I am able to ping and nslookup autodiscover without issue.  I will run the connectivity test later today.
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Accepted Solution

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compcreate earned 0 total points
ID: 40254059
The two problem PC's were actually using the 365 subscription for Outlook.  We got the solution from MS which was to run the connectivity analyzer (which passed on both machines), then grab the server name for logon that is shown on the analyzer (unique to each PC), no do the manual setup of outlook anywhere as normal but put the copied address in for the server instead of the normal server name like exchange.domain.com and then it worked fine.  Clearly some sort of bug with MS that it doesnt autodiscover and populate that info when you set it up the normal way.
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Author Closing Comment

by:compcreate
ID: 40264823
This was the proper solution provided by MS directly.
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