Third Party Applications August 9, 2004 at 7:00 am

Using Entourage 2004 for Exchange Connectivity

Sick of being stuck with Outlook 2001? Then Entourage 2004 might be a way out of Classic mode. I’ll even tell you how to convert those nasty .pst and .pab files. Two for one in the third party app department today! (Updated 8/11/2004)The Exchange Problem

Blighting our Mac computing landscape is the beast known as Exchange. Because of so many CTOs drank the MS marketing kool-aid; it would seem that Exchange is rolled out just about everywhere Active Directory is in place. I’m not going to get into my grievances with Exchange, and its client Outlook, here though. I’m just going to try and help you get through it.

Some Grievances

I never said I didn’t have some grievances about the whole situation did I?

  1. MS made us languish with Outlook 8.2.2 for years.
  2. MS released the fairly good Outlook 2001 to replace 8.2.2 in , um, 2001.
  3. MS has made us languish with Outlook 2001 in Classic mode for years.
  4. MS promised the world with Entourage X and we fell for it.
  5. Entourage X was an awful Exchange client.

See a pattern here? Unlike IBM which keeps Notes up to speed on the Mac (I’m not a fan of Notes either here, so that’s not an endorsement.) Microsoft has punished Mac users for years in predominately Microsoft shops. While Entourage 2004 isn’t everything that we deserve from Microsoft, it is more than I have grown to expect.

Entourage 2004

Entourage 2004 delivers many of the features that were lacking in Entourage X. Let’s be clear though, it is not a full Exchange client like Outlook.

The Good Stuff

Entourage 2004 only requires LDAP and WebDAV to be active on the Exchange server. Since LDAP is part of Active Directory and most Exchange sites use the Outlook Web Access (OWA) you are probably good to go. Note that it has the same basic server requirements of Entourage X (At least Exchange 2000 SP2.) just without the IMAP and SMTP needs. Basically Entourage 2004 functions as a really spiffy OWA client. There are other products that take this same approach, like Evolution, but they don’t seem to feature the same polish, support, and acceptance that Entourage does.

Assuming your DNS and Exchange server are functioning properly setup is a breeze. Simply enter your e-mail address, username, password, and domain in the Account Setup Assistant and it does the rest. When done it even has a test button that will double check the settings. If you are using special settings like SSL or HTTPS you will probably need to configure some settings in the account by hand.

Once it is setup Entourage will sync up to your Exchange account. This includes mail, contacts, and calendar events. There is no real way to control the schedule of the sync. The syncing that does occur performs as follows :

a) On account setup.
b) On launch.
c) Every 5 minutes.
d) After every local change to info there is a 1 minute countdown and sync. If you make another change before that minute is up, the countdown resets.

So you can fake it by launching the app or making a change, but it’s probably just best to wait 5 minutes.

Mail is easy to use and feels just like mail in Outlook XP. I do admit that I like the 3-pane view that Entourage 2004 has.

You can browse and subscribe to public folders on the Exchange server. The public folder location should setup automatically, but you can change it if needed in the Advanced tab of your Exchange account settings.

Contacts are simply synced. Only contacts in the top level of your Outlook contacts folder are synced, and only the first 3 e-mail addresses attached to a contact in Entourage are synced to the server.

Calendar events are synced as well and the event window now properly updates the free/busy status of all participants in a meeting. Outlook 2001 didn’t even do that. You can invite other users to your event and their status is updated in your calendar appropriately. Additionaly, users can invite you to events and those events are added to your schedule if you accept them.

In response to a real sore spot in Entourage X, you can be a delegate now and have access to someone else’s calendar, mail, and contacts. However if you want to delegate to someone else a trip to OWA or Outlook is required, which brings us to our next section.

The Bad

There really isn’t too much wrong that I can find with Entourage 2004, but there are some points of friction.

When doing scheduling it seems that you must use the “accept with notification’ and that people you invite must do the same. If you invite an Outlook user, and they accept without response then your event is never updated in Entourage. The free/busy for that user will show that they are doing something, you just can’t tell it is with you.

Also scheduling gets a bit strange when you are invited to a meeting. Say Joel (Having lost his mind and switched AFP548 to IIS and Exchange.) sends Steve Jobs and myself an invite. I can accept the invite and it will appear in my calendar. If I go look at the event details though I will see that the attendees are Josh, Steve, and Josh. So what is going on here?!? Here is what seems to be the problem:

a) I receive the invite from Joel.
b) I click accept and Entourage makes an event in my Entourage calendar.
c) Because Entourage created the event for me to see in my own calendar, on my own Mac, I logically must be the owner of said event.

Entourage knows that I didn’t create the event because if I were to try and change it it will remind me that I don’t own it and that any changes the event organizer make will overwrite my own. It is an easy enough thing to overlook by the third meeting you accept, but it seems like it would be an easy fix to make the event indicate that it was created by the person who sent the invite.

There is no out of office assistant or any other access to server side rules. If you want to use these features you need to login to OWA and do it in your browser. Bleh.

There isn’t good error reporting from the server. I tried to send a mail the other day only to get a very generic “The HTTP server could not complete the request.”. I logged into OWA, tried to send the same message, and was given a very pleasant “You are over your mail storage quota. No mail can be sent until you clear out some space.” sort of message.

You can’t browse the full GAL, you need to type part of the person’s name to narrow the search down first. I really don’t care about this one.

When addressing an e-mail you are forced to use the check names feature to complete e-mail addresses. This really isn’t that bad as searching a huge LDAP db takes too long when addressing mail in my view. I tried using Apple’s Mail program for a comparison here and it sucks when it takes over a minute to type each e-mail address.

When using public folders you can only see e-mail messages. You can also only use existing folders, you can’t create or modify them from within Entourage. You can not post directly to a public folder, you either need to send it an e-mail message or drag an e-mail into the folder. Lastly the master public list isn’t cached so it has to refresh every time you click on it. If you have a ton of public folders this can take a long, long time. Subscribing to specific folders will help greatly here.

Hey! Didn’t you mention PST and PABs?

Why yes I did! For those of you that don’t know .pst and .pab files are Microsoft’s way of storing e-mail and addresses locally. The main benefit to Microsoft here is that it locks all of this data in an impenetrable fortress of a file that no developer has seemed to crack yet. However there are three ways that I know of to get this data from your Outlook client (2001, 2000, XP. They are all the same with the exception of 8.2.2.) into Entourage. Unfortunately the two best options require a PC, although VPC will work fine.

  1. You could upload all of that mail to the server and then re-download it again. This is the official MS way and is about as stupid as you can get. The reason that most people have a pst in the first place is that they have more mail than the server will allow.
  2. There is a byzantine procedure that involves moving the pst to a Windows box, importing it into Outlook Express, importing that into Eudora, then processing the resulting mbx files into mbox files with some $20 shareware AppleScripts. Then you can drag and drop the results into Entourage. It should be noted though that this method will not import contacts or e-mail attachments.
  3. The best method I have found is a commercial product from Little Machines called Outlook2Mac. This $10(!) application runs on a PC and will convert whatever you want into mbox files that you can drag and drop into Entourage or any other Mac OS X mail client. It has a lot of flexibility and can export by folder and date range. It also will export with attachments and gives you the ability to filter the export by size and file type. Lastly it will do your contacts as well. $10 well spent to get away from Outlook 2001 in my opinion.

Wrapping it up

With Entourage 2004 Microsoft has at given Mac users an Exchange client that is at least tolerable under Mac OS X. While it may not be that full MAPI client that we all long for to use with Exchange it is far better than Entourage X or Outlook in Classic mode.

If you want some good reading on how Entourage 2004 works, along with troubleshooting info, you should download Microsoft’s Office 2004 Resource Kit. It is a good read if you will be supporting Entourage in an Exchange environment. You can also just download the Entourage section of the resource kit, Working with Exchange.

No Comments

  • I like Entourage but not 2004. The version that came with Office X
    which is 10.1.0 is definatelly better. I here at work i have well over
    90,000 emails and searches within Entourage 2004 are so painly slow.
    I’m planning to move to Apple Mail or just revert back to 10.1.0.

    I think this needs to be fixed in 2004.

    Gulp! 90,000 mails on the Exchange server? I would imagine that
    the slowness might come from the fact that 2004 uses OWA for doing mail
    and X used IMAP.

    You could always try setting it up as an IMAP/SMTP account and

    Apple’s Mail will use the same IMAP/SMTP strategy with a few wrinkles. It
    should pickup incoming event invites and convert them to ics files for use in
    iCal. It should even give you the option of sending a response,

    If you tell Mail that it is using an Exchange account it will hide the IMAP
    folders that exist for your schedule events. If you use mail rules it can mess
    with these hidden messages and you won’t be able to put them back where
    need to go!

  • Actually, it’s the same price to have Outlook for the PC or Mac, insomuch that you have to buy the Office Suite. The free version you mention is Outlook Express, which is not a native Exchange Client. Office for the PC or Mac is $149 for student/ed. or $399 for standard, so I’m not sure what your beef is there.

    As for other possible bads, did you happen to find out if DLs synch up in Ent. 2004? It didn’t work in Ent X.

    • Thanks for pointing out my pricing problems. Outlook used to be a free
      download for Mac and PC since Exchange used to be server side licensing.
      Now you need to purchase the basic Exchange license and CALs. Each CAL
      starts at $63 and comes with Entourage or Outlook.

      I’ll amend the article.


  • Macshome, you didn’t mention Public Folder which is the only thing I don’t
    like in Entourage 2004. You have to subscribe to every single subfolder on
    the server, and even so, it doesn’t sync properly.

    • Hmm.. I just tried it and I can subscribe to any particular folder that I care to
      on the Exchange server here.

      It is true that it needs to lookup all of the folders every-freaking-time you
      select the public folders, but after you subscribe you shouldn’t need to go
      back into the master list.

  • I think it’s worth noting that Entourage 2004 won’t sync with Exchange NT.
    Apparently. So until our IT dept is bent over for Exchange 2003, we’re stuck
    with OWA.

    Also, our GAL has 20,000 users (give or take) and my autocompletes
    addresses timely, whereas Entourage requires the "check names" button;
    that’s one of main reasons continues to be our recommended mail

    If if takes your one minute, that’s either a much larger GAL or a
    slower LDAP server (or connection.)

    • Hmm.. I’ll clarify the section about the system requirements. I said they were
      the same as Entourage X, but never said what those were! (At least Exchange
      2000 SP2)

      I’ll try Mail again and see what the addressing latencies are like. Remember
      you can set Entourage to auto check names when you hit the send button.

    • I keep hearing people saying that they need to click the “check names”
      button. It used to happen to me, but no more. I don’t think our Exch2003 has
      different setup than others. But I do have these two settings turned on in
      Entourage preference:

      “Automatically check names when sending messages” and
      “Display a list of recently used addresses when addressing messages”

      Hope it helps.

      • Thanks for listing the exact settings. That was the point I was trying to make in my last post, but this will clear it up further for people trying to find the settings.


        Breaking my server to save yours.

        Josh Wisenbaker

  • Well, I would of at least investigated it myself in my customer’s setup. I, and my
    70 or so designers I support, use it all day, every day, for e-mail and
    calendaring. So does the Microsoft MacBU. So does lots of other clients I’ve had
    that I setup with Entourage 2004 as Exchange clients.

    What in particular from the post scared you off?

    Breaking my server to save yours.

    Josh Wisenbaker

  • We have implemented Symantec E-Vault for email archiving, and would like to be able to prevent users from saving mail to their local folders so that all email is archived properly.

    Thus far, I have not been able to either disable, delete, or hide "Folders on My Computer" and wondered if anyone had a workaround for this?

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