In recent years, Microsoft’s Exchange Server and Outlook client have emerged as the leader in the messaging and collaboration platform marketplace. However, it was not until version 5.5 that Exchange really gained a wide acceptance among businesses. In fact, that version was so popular that there are still many Exchange 5.5 installations running in businesses throughout the globe.

However, while a lot of companies have not been able to justify the upgrade to Exchange 2000 or 2003, many of them have upgraded to newer versions of Outlook when upgrading installations of Microsoft Office. As a result, the Exchange administrator is now faced with the dilemma of making a newer client work with older messaging software. This can lead to a number of problems when using Outlook 2003 to access a mailbox on an Exchange 5.5 server.

I’m going to outline some of the more common problems that Exchange administrators might run into as they deal with a mixed environment of Exchange 5.5 and Outlook 2003. We’re going to look at:

  • What the problem is
  • What Microsoft recommends to do
  • Where to find any applicable patches

Problem 1
Perhaps the most common issue being reported by Exchange Administrators when dealing with Outlook 2003 and Exchange 5.5 cohabitation is the issue described in TechNet article 818709. One of the most useful and heavily used features in the Exchange feature-set is Outlook Web Access (OWA), or the ability to access an Exchange mailbox over a Web mail connection.

According to Microsoft, when you use OWA to access a mailbox on a server running Exchange 5.5 and you are using a user account that was previously accessed from a client computer running Outlook 2003, your OWA may stop responding.

If you monitor your event logs, the event listed below will show up on the Exchange system that the client was attempting to access:
Source: MSExchangeISPriv
Event ID: 2078
Description: Unable to submit, send, or transfer out a message.
Check PR_Recipient_Number, PR_Recipient_Type, PR_Report_Type

The reason this problem occurs is due to an additional multivalued attribute that Microsoft has added in order to facilitate some newer features. When you use an Outlook 2003 client it adds a fourth entry to this attribute (three is the normal) and then when you try to access your mailbox via the Web (after you used an Outlook 2003 Client), OWA and the server cannot effectively deal with the additional attribute, and in turn decides to quit playing.

There is a patch available, but this patch is only available for people actually experiencing this problem. Consequently, you have to contact Microsoft directly to be able to download it.

Problem 2
If you are like me, then the quantity of e-mail you receive on daily basis can quickly pile up. Being able to organize these messages in a way that allows you to locate them at later date can sometimes be challenging. One newer feature that Microsoft has added to the post-Exchange 5.5 world is the ability to apply filters to a folder. This nifty little feature can quickly be a go-to maneuver when trying to locate a particular message or group of messages.

However, for those who might attempt to use this feature from an Outlook 2003 client that is connecting to an Exchange 5.5 server, you will be disappointed. Exchange 5.5 does not support filtered views on Outlook search folders, which means that you can’t leverage this on your Exchange 2003 Client. If you attempted to perform this feature, the results of your search would simply be a bunch of empty items in the Outlook search folder.

You could upgrade your servers, but let’s be realistic; chances are this feature alone does not provide a valid enough business incentive to perform an upgrade. Alternatively, you can use the workaround our friends at Microsoft have provided (the following is an excerpt from TechNet article 817955):

To work around this behavior, create a custom search folder and specify what you want to be filtered in the criteria for the custom search folder. For example, you can create a custom search folder for all the unread e-mail messages that you received today, instead of trying to apply a filtered view on the Unread Mail search folder.

To create a custom search folder, follow these steps:

  1. On the File menu, select New, and then click Search Folder.
  2. In the New Search Folder dialog box, click Create A Custom Search Folder in the Select A Search Folder box.
  3. Under Customize Search Folder, click Choose.
  4. In the Custom Search Folder dialog box, type a name for your custom search folder in the Name box, and then click Criteria.
  5. In the Search Folder Criteria dialog box, select the options that you want for your custom search folder, and then click OK. For example, type unread mail received today.
  6. On the More Choices tab, click to select the Only Items That Are check box. The Unread option must be selected in the box that is next to this selected option.
  7. On the Advanced tab, click Field, select Date/Time fields, and then click Received.
  8. Click Today in the Condition box, and then click Add To List.
  9. Click OK to close the Search Folder Criteria dialog box.
  10. In the Custom Search Folder dialog box, click Browse.
  11. In the Select Folder(s) dialog box, select the folders that you want to search, and then click OK.
  12. In the Custom Search Folder dialog box, click OK.
  13. In the New Search Folder dialog box, click OK.

Don’t plan on seeing Microsoft do anything to change this either. In fact, the words ring loud and clear in the TechNet article: “This feature is by design;” which is a cryptograph for, “We are not going to fix this so use the workaround!”

Problem 3
Keeping with the theme of “unusual” searching characteristics, this next issue follows suit with problem number 2. If you are using Outlook 2003, and it is connected to Exchange 5.5; and if you utilize the Search feature to search for a specific item; and if you decide to try to delete one of the folders that your Outlook 2003 client is searching for; then, you will possibly experience the following two symptoms:

  • The deleted folder will still appear in the results list of your search; and
  • You receive the following error message: “Unable to Display Folder.”

This issue (TechNet article 820717) is really a nonissue, but sometimes from a user’s perspective, it may seem to be malfunctioning. If you really stop to think about this, the Outlook 2003 client is essentially trying to look into a folder that you deleted. Of course it can’t, so it pops up an ominous error. If anything, the method of notification is the only thing at fault here. Perhaps Microsoft could explore another, less intimidating, notification method, but it is unlikely that it will do this. The Exchange administrator should approach this issue from an educational point of view. Help your users understand this behavior and train them to avoid it.

Problem 4
Here we will find a problem somewhat similar to (and often confused with) issue #1. This problem might manifest itself when using Outlook 2003 to modify rules when importing those rules into a mailbox that is located on an Exchange Server 5.5 server. When you attempt to execute the previous rules, the Exchange Information Store service will unexpectedly stop responding. This is a result of your server experiencing what Microsoft calls a “malformed property.” Essentially, newer attributes are handled incorrectly by the older messaging server.

If you haven’t been able to figure out that you have a problem when your Information Store stops responding (let’s hope you can), then you can also look for the following error in your Exchange server’s event log:
Event ID: 4097
Source: Dr. Watson
Description:
The application, exe\store.dbg, generated an application error.
The error occurred on date @ time. The exception generated was
c0000005 at address 0042456d (EcDSDNFromSz).

TechNet article 8249418 provides a link to a fix that is available for this problem. I’d like to point out an important note as far as applying this particular patch: You must stop the Information Store Service prior to installing the patch.

Miscellaneous issues
Here are some additional issues that you may experience infrequently:

  • You might run into some problems with Outlook 2003 if you upgrade your Exchange 5.5 server to Exchange 2000. Check this link for more info.
  • On a similar vein as the issue discussed in Problem 1, this link is provided. Essentially it is the same problem but on Exchange 2000 instead of 5.5.
Helpful links

From one Exchange administrator to another, I’d like to pass along some helpful links. Some of these you may already know, and I am sure that I have left out some good ones, but here are a few links that have served me well:

Summary
As with any software, there are sometimes issues that may arise when attempting to provide support for legacy applications. Such is the case when mixing Outlook 2003 with Exchange 5.5. Does this mean you shouldn’t run the combination? No, certainly not. Instead it means that you, as a vigilant Exchange administrator, must be proactive to identify and rectify any of the issues you experience before they spin out of control. Education and proactive monitoring can go a long way toward keeping these problems under control since all of the problems mentioned in this article can be resolved, or at least mitigated to some extent.