Entourage and Issues with Delegated Mailboxes. OWA?

As you might guess from my articles, I am a Windows guy by trade so anything Mac is a learning experiencing for me. I had a few Mac workstations that needed to access a shared Exchange 2003 mailbox using Entourage 2004. After working with Entourage for an hour, I started to realize why some people call it erage. Microsoft pawned off the Entourage product to the Mac development group and apparently left them in a design vacuum with minimal help from the Microsoft Office and Exchange teams. (or something like that)

Entourage uses Outlook Web Access (OWA) to connect to the Exchange environment. This isn’t just any version of OWA, it’s a specific version, the older clunky version that you would never want to use in a production environment as a webmail solution. When you add an Exchange account to Entourage, you are required to provide an Exchange server name (obviously) which Entourage takes and creates the OWA URL for accessing the mailbox. The issue seems to be that Entourage uses a defined URL generation function that may or may not work correctly with your Exchange environment. I found this to be particularly true when trying to add shared mailboxes as a delegated mailbox into a primary account.

In my particular case, we had some shared mailboxes that would not connect correctly. After adding them to the “Users I am a delegate for” list, I could not see the Inbox, regardless of the permissions that were set. What was more interesting Some accounts it worked fine for.

So what is the fix?

Let’s start by understanding Entourage and its unique relationship with OWA. If you open a web browser and point it to http://[your exchange server]/exchange/, what do you get? On a domain joined computer you should see OWA and your mailbox. In Entourage, when you provide only the Exchange server name, Entourage builds the URL similar to the one above. This works great as you are able to view the default content, which is your mailbox.

Now, what about when you add an item to the “Users I am a delegate for” list? How does Entourage build the URL for accessing something other than the default content, which is your mailbox? Easy! Just put a unique identifier following the /exchange/ directory in the URL, http://[your exchange server]/exchange/aaron/. Wait if it were THAT easy, I wouldn’t be writing this article.

The issue is that Entourage builds a URL that may not match what is defined in the Exchange environment. Luckily, Entourage lets you type the full URL if you happen to know what it is, just in case the URL generation function screws up.

There are two ways to connect to another account using OWA:

  1. http://[your exchange server]/exchange/[unique identifier ?? for your account]/
  2. http://[your exchange server]/exchange/[default SMTP address]/

The reason I put two question marks in the first option is because I have yet to determine where this unique identifier is stored and what decides what it is (can someone enlighten me?). This is where the failure might occur; Entourage uses the top one by default when creating the URL, so if Entourage thinks your unique identifier is “aaron” but Exchange says its “aaron.devtrends”, then Entourage isn’t going to be able to connect to that mailbox. This is unfortunate as it complicates adding a mailbox to the “Users I am a delegate for” list. But, at least there is a solution.

The resolution is to use the second option of URL generation scripts. In the Exchange properties, you can set the Exchange server to the full path of the specific mailbox that you want to open:

http://[your exchange server]/exchange/[default SMTP address]/


Replace [your exchange server] with your Exchange server name and the [default SMTP address] with the default SMTP email address of the mailbox you are trying to open. As you test this, be sure to be patient with replication if you are in a multi-site domain; this being true if you just added or changed an SMTP address. Otherwise you may see error 18597 or HTTP errors.

As a last note, I’d recommend testing the URL in Safari prior to saving it in your Entourage configuration!

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