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Outlook finding mailbox server settings

Posted on 2013-01-07
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Last Modified: 2013-01-14
Hi, when assigning a user a mailbox I get the following problem:

1. Through Outlook automatic it finds user@mail1.org.local, click next
2. Goes to "search for user@mail1.org.local" server settings, errors out
2. Exchange messagebox comes up with Servername & mailbox name.
  2.a If I put in the exchange server name (mail1) and click on check name it bombs out
  2.b If I put in the GC from that site IP address (192.168.0.1) and click on check name, the server name changes back to mail1.org.local and after an extended period of time it works.

I have looked in the DNS settings and the autodiscover points to IP address of mail1, the MX record points to exchange server name.
Can anyone shed anymore light on this issue?
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Question by:Ozwazza
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by:jodiddy
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I have a couple questions for you!

What version of Exchange are you running?
Is Outlook Anywhere configured?

For autodiscover to work correctly Outlook Anywhere needs to be configured properly as well.

I'm assuming you have a single Exchange Server, then all your A records should point back to that Exchange Server IP.
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by:Ozwazza
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Exchange 2010, just upgraded over the weekend from 2007, the old server was removed before update occured, after which I disovered was not a good thing to do.

Using outlook 2007 & Outlook 2010.  Outlok anywehre has been enabled, don't really know if its been configured properly, is there something I can do to test.

yes all A records point back to exchange server (I am assuming autodisocver - 192.168.1.1
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jodiddy earned 500 total points
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Yes, you should have allowed the clients to update prior to decommissioning your 2007 server. Well we live and learn.

What URL did you specify for Outlook Anywhere? autodiscover?

yes there is a test you can perform.

In the Exchange 2010 Tool Box there is the Remote Connectivity Analyzer tool.  You can use that to test Outlook Anywhere, Active Sync and other remote exchange services.

It's just sends you to a website:  Remote Connectivity Analyzer
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by:Ozwazza
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Url for Outlook anywhere is external mail address (mail.domain.org.au) with NTLM authentication. Where would I find the autodiscover?
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by:jodiddy
jodiddy earned 500 total points
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autodiscover is used by Outlook, when it uses Outlook Anywhere to find your site you need to have a DNS entry for autodiscover in order for Outlook Anywhere to work, you don't have to set it anywhere.  That needs to be setup both internally and externally.

Outlook Anywhere should have a separate URL, like anywhere.domain.org.au for example and not just be your regular mail server domain. Then you would need a DNS A record entry for anywhere.domain.org.au for example, pointing to the IP of your Exchange Server.

When you enabled Outlook Anywhere it asked you for a URL correct?

So you should have the following urls.  

Your Exchange Server is @ 192.168.18.2 (internally), and externally @ 206.55.55.55

anywhere.domain.local - 192.168.18.2
mail.domain.local - 192.168.18.2 - plus a DNS entry for the FQDN
autodiscover.domain.local - 192.168.18.2

external DNS Records:

anywhere.example.com - 206.55.55.55
mail.example.com - 206.55.55.55
autodiscover.example.com - 206.55.55.55

Plus an mx record probobly - mail.example.com
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Author Comment

by:Ozwazza
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Autodiscover - 192.168.1.1 is in DNS
I've jsut put mail.domain.local - 192.168.1.1 into DNS and anhwyere.domain.local - 192.168.1.1 into DNS


The other interesting issue, when I do aa get-GlobalAdddressList|FL is shows the default GAL but with the originating server as the old 2007 that I removed, is that an issue?
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by:jodiddy
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So did those fixes resolve the issue with Outlook?

Yes, your going to need to get the GAL situation resolved as well.

OAB Generation Server, where EXCHANGE2010 is your Exchange Server:
Move-OfflineAddressBook - Identity '\Default Offline Address List' -Server 'EXCHANGE2010'

Open in new window


You are also going to have to upgrade your address lists

All Users default address list

Set-AddressList "All Users" -IncludeRecipients MailboxUsers

Open in new window


To Upgrade ALl Groups default address list

Set-AddressList "All Groups" -IncludeRecipients MailGroups

Open in new window


To upgrade All Contacts default address list

Set-AddressList "All Contacts" -IncludeRecipients MailContacts

To Upgrade Default Global Address List

Set-GlobalAddressList "Default Global Address List" -RecipientFilter {(Alias -ne $null -and (ObjectClass -eq 'user' -or ObjectClass -eq 'contact' -or ObjectClass -eq 'msExchSystemMailbox' -or ObjectClass -eq 'msExchDynamicDistributionList' -or ObjectClass -eq 'group' -or ObjectClass -eq 'publicFolder'))}

Open in new window


To upgrade Default Email Addrses Policies

Set-EmailAddressPolicy "Default Policy" -IncludedRecipients AllRecipients

Open in new window


You will need to set it for each Mailbox Store once you have it generated by going to Mailbox under Organization Configuration and right clicking the MDB and selecting properties, then go to the Client Settings tab seen here: Exchange MDB properties
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Author Comment

by:Ozwazza
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Hi, fixes did not resolve with Outlook.  Still cannot download the global address list.  Can't move the offlineaddressbook to anywhere because there is only one server.

The Microsoft Exchange Address book service is not turnng on, I click start and the process starts then stops straight away, is that anything to do with it.
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Expert Comment

by:jodiddy
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Yes, I'm sure the fact that the Exchange Address book service not starting has something to do with it not being able to download the GAL.

Did you fully decommission the Exchange 2007 server, or just shut it down?

Basically your looking at two separate issues.

Outlook - Finding Exchange fast
Outlook - downloading GAL

The two are most likely related.

Sounds like there are some internal Exchange issues happening.  Have you checked the Event Logs on your Exchange Server, do you see any errors or warning related to Exchange?

Also after Outlook finally connects to Exchange, please check the connection status and verify the URL's are all correct.  You can do that after Outlook is running by holding the right-ctrl key and click the Outlook icon in the system tray, then select Connection Status.
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Assisted Solution

by:Ozwazza
Ozwazza earned 0 total points
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Solved my problem, the Microsoft Address book service was not loading, after researching I found this article:
http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/2d55edb0-8e34-4e02-b87b-d66f725deaf8/?prof=required

Cleared the registry and restartted the server, loaded the service and evertyhing works great.  I was going to reinstall 2007 and work backwards but I gave the test autoconfiguration one more try and the result passsed so then did a little more work and found the service issue.  Thank you for guiding me in the right direction
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Author Closing Comment

by:Ozwazza
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Fundamental reason why it was not working was because the Microsoft Address book service was not working, although would not have persevered unless guided by other experts comments
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