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Simple ways to troubleshoot Exchange Offline Address Book problems

After deploying Outlook 2013, a common problem administrators may encounter is that of impaired Exchange Offline Address Book functionality. Specifically, the Offline Address Book may fail to download to Outlook 2013 clients. But there are several steps you can try to correct it.

Public folder problems

The vast majority of Exchange

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Offline Address Book problems you're likely to encounter after an Outlook 2013 deployment are related to public folders. The main issue is that legacy versions of Exchange Server use public folders for Offline Address Book distribution. Outlook 2013 doesn't support public-folder-based Offline Address Book distribution because of Microsoft's efforts to move away from public folders. Configuring Exchange Server to use Web-based Offline Address Book distribution will address this issue.

Web-based distribution is a Client Access Server function. Outlook contacts the Autodiscover Service to determine the closest Exchange Offline Address Book distribution URL before determining the most appropriate URL to pass to the Outlook client. Outlook then connects to the URL and downloads the Offline Address Book.

Although this process sounds simple enough, its success depends on proper configuration. There are a number of things that cause problems with Web-based distributions.

Incorrect Exchange Offline Address Book versions

As I mentioned at the beginning, you're most likely to experience problems if you connect Outlook 2013 to a legacy Exchange Server environment. One of the reasons for this is that Microsoft has introduced multiple versions of the Offline Address Book over the years. Outlook 2013 only works with version 4 of the Offline Address Book, which was introduced in Outlook 2003 SP2. If you're running something older than Exchange 2007, there's a chance you're using an incompatible Offline Address Book format.

Another Exchange 2007 glitch

It's worth noting that Exchange 2007 had a glitch that caused the Enable Web Based Distribution checkbox to be grayed-out on the Default Offline Address Book Properties sheet. This glitch prevented Outlook 2013 clients from being able to download the Exchange Offline Address Book. To fix this problem, open the Exchange Management Shell and enter the following command to enable the checkbox:

Set-OfflineAddressBook "Default Offline Address List" –ApplyMandatoryProperties

Conflicts with URLs

The problems we've discussed so far only occur in situations when using Outlook 2013 in a legacy Exchange Server environment, but Outlook 2013 can have trouble downloading the Offline Address Book even in an Exchange 2013 environment. This can happen if Client Access Server using the OAB virtual directory is not properly configured.

One of the most commonly reported problems in Exchange 2013 environments is when external users are not able to download the Offline Address Book. This problem can often be attributed to a mismatched or incorrectly configured URL. Exchange Server 2013 allows you to set a URL for internal Exchange Offline Address Book access and a separate URL for external access.

To determine the URLs currently used, open the Exchange Management Shell and enter the following command:

Get-OABVirtualDirectory "OAB (Default Web Site)" | Select-Object InternalURL, ExternalURL

Exchange does not configure an external URL by default (Figure 1). You can set an external URL by entering the following command:

Set-OWAVirtualDirectory "OAB (Default Web Site)" –ExternalURL https://<your domain>/OAB

You would replace <your domain> with your domain name in the above command.

So what do you do if the correct external URL is listed but external clients are still unable to download the Exchange Offline Address Book? There are several things you should check:

  • Make sure your Client Access Server is configured with a valid SSL certificate.
  • Make sure the Outlook client computers trust the certificate authority that issued the certificate.
  • Make sure your DNS server contains the correct records.

About the author:
Brien Posey is an eight-time Microsoft MVP for his work with Windows Server, IIS, Exchange Server and file system storage technologies. Brien has served as CIO for a nationwide chain of hospitals and health care facilities, and was once responsible for IT operations at Fort Knox. He has also served as a network administrator for some of the nation's largest insurance companies.

This was first published in October 2013

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