Faking Exchange Support in OS X Leopard

I recently took the plunge and bought the new MacBook Pro (well my company bought it for me).  The workflow is completely different and frustrating at times, but when you get the hang of it it’s worth it. My iPhone experience was so positive that became a victim of the “iPhone Halo.”

That being said, making the migration is painful in some areas. One of which was how I handle the lack of productivity software I had in Windows—namely Microsoft Outlook.  As I search around there are a few options in attempting to tackle this problem.

  1. Use VMWare Fusion or Crossover to load Windows and then Outlook.
  2. Use Microsoft Entourage.
  3. Find a way to use the native OS X applications (iCal, Mail.app, and Address Book).

Using Virtualization Technology

This seems straight forward enough on the surface, but on the inside it’s fraught with problems.  First, the idea of using a virtual machine to load productivity software doesn’t seem, well, productive.  This is especially true when I have to dedicate a gig of precious memory to the VM (granted I have 4 GB).  I tried it, and I was able to use it without problem but I wasn’t happy with this option.  I became discontent with it when I started using Mail.app for my personal e-mail. I love the simplicity of the application, and I wanted to use it full time.  I should say I tried Crossover, and I didn’t like it at all. VMWare’s unity feature is far better.

Use Microsoft Entourage

I went out and got a license of MS Office 2008 for Mac.  Word, Excel, and PowerPoint aren’t bad, but they pale in their Windows counterparts. After using the ribbon for so long now I love it. Office 2008 has a “ribbon” of sorts, and it’s not that bad. For quick document work it works fine. If I need more then I can use my virtual machine. However, this isn’t the case for Entourage.

Microsoft Entourage has to be one of the worst e-mail clients I’ve ever used. Sure, it connects to Exchange without a problem, but when you have expectations it will work like Outlook it is very disappointing.  I tried it for a while, and I decided it simply doesn’t cut it. The way you add recipients in e-mail is awful, and I quickly found out that you can’t do HTML e-mail in Entourage which means no embedded links. Epic fail. I hated it, and it made me look to the third option.

Faking Exchange Support

I say “faking,” because the support isn’t native to the OS X apps. Recently, Apple unveiled that the next version of the OS dubbed “Snow Leopard” will have native support for Exchange 2007 in their apps similar to the iPhone (which I use without complaint). But right now my company uses Exchange 2003 which I don’t know if it will be support in Snow Leopard, and it isn’t to be released until next summer.  That leaves a long time for frustration. Surely, there must be a way to do this right?

After searching extensively I discovered I’m not the only who has struggled through this. What surprises me even more is the lack of a third party vendor to fill this void. I would’ve happily paid several hundred dollars for this, but there is nothing out there to accomplish this. It is obvious that only until recently is Apple taking the enterprise environment seriously with Exchange support (no matter how much they may despise it).  I fortunately was able to find a solution in the mean time. Here is my recipe:

Ingredients

  1. Microsoft Entourage (bear with me)
  2. Mail.app
  3. IMAP enabled in Exchange
  4. Dock Dodger

Preparation

The preferences pane in Entourage

The preferences pane in Entourage

I discovered that Entourage supports sync services to send calendar events and contacts to the native OS X programs. OK, this is a good start.  As you can see in the screenshot go to Entourage – Preferences and select Sync Services in the left panel.  Then check both boxes to send calender events and contacts to the native applications.  This will via a background service take care of the synchronization from the native apps to Exchange. When you select the option to sync you will receive a prompt, and you will want to choose “Merge Entourage items with Sync Services items” which will allow bi-directional sync between the two. So if you add an event in iCal it will go to Entourage and then Exchange, and if I add an event in my iPhone it will go from Exchange to Entourage to iCal. Not pretty but it works.

Then we have the e-mail issue. This was by far the most difficult and frustrating part. When you create accounts in Mail.app it allows you to create Exchange accounts which is a misnomer. What it means is it will attempt to use Outlook Web Access to send/receive, but it also means you’ll be really using IMAP on an Exchange server.

I found an article which outlines setting up IMAP on Exchange. I had to sweet talk my boss, and he sympathized and helped.  They set up IMAP (Exchange is above me), and that led me to now getting closer to being free of Entourage.  When you set up an account under the Exchange heading you’ll be asked to specify a mail server (such as mail.yourdomain.com) which will come from your Exchange admin. You will also give it the address where you access Outlook Web Access (your webmail address). I was then able to successfully download messages. I had some problems with SMTP. My company uses RPC over HTTPS to connect so I had to use the Password option and specified my credentials (for the username I had to use domain\username).  Then I was up and running!

Cleaning Up

Now it’s working. It’s not pretty, but I wasn’t expecting it to be. It was a utilitarian effort, and it succeeded in accomplishing my goal. But it wasn’t as seamless as I wanted. Entourage would always show up in the dock and also the application switcher. Now I never want to see Entourage anywhere, and I found Dock Dodger. This is a freeware program that removes running applications from the dock and application switcher. By simply dragging the Entourage icon into the app it removed it. Before I did that I click on the icon in the dock and decided to open it at login (as I’ll always need it).

You’ll also notice dialogue windows for the send/receive. I haven’t found a way to completely remove them, but if you close it when it’s running it will go away. Unfortunately, on reboot it comes back. I hope to find an answer to get rid of the dialogue.

Concluding Thoughts

I can now use the native apps, and I am up and running. Entourage now uses around ~75 MB of memory which is much better than the 1 GB option with VMWare Fusion.  I am happy for now, and I look forward to Snow Leopard when I can completely axe Entourage from my life.

I would like to thank Nick Dawson (my Pownce buddy) for empathizing with my struggle and pointing me in the direction I needed.

15 Responses

  1. Nick November 4, 2008 / 12:53 pm

    Great post – really sums up the 3 major options well!

  2. Jason Belec January 14, 2009 / 8:22 pm

    Wonderful post! It allowed me to help a few people that were frustrated by the crippled apps from MS on the Mac.

    Thanks for sharing.

  3. Rich February 6, 2009 / 10:23 am

    Great article, the best I’ve found. However, as it was so good, and I feel I totally understand my options, I think I’m going to struggle on with Outlook Web Access for now and hope Snow Leopard comes out soon!

  4. Donald Jemela July 20, 2009 / 12:46 am

    Will this keep all email folders synchronized or just receive mail to the inbox? For instance, on my windows machine I create a folder for email called “Keep”. Will that folder be automatically created in Mail.app? And when I use outlook on my pc and drag an email from my inbox to “keep”, will it automatically be in Keep folder on Mail.app? And last, does this bring tasks and notes from exchange to the mac native app?

    • Chris Poteet July 20, 2009 / 1:57 am

      @Donald: IMAP will only synchronize inbox. Entourage will synchronize other folders if they’re created on the server and not in separate personal folders. And no notes and tasks aren’t synced to Mail.app; however, that will all change in Snow Leopard due out in September.

  5. Donald Jemela July 24, 2009 / 1:09 am

    Thanks Chris. That seems like a lot for me to try. One thing I was wondering: If you have Entourage “hidden” but you are still depending on it, how are you able to tell if Entourage is connected to the Exchange Server? For instance, when I close my laptop and then open it back up, how would I know whether entourage connected successfully and everything is sync’ed?

  6. Peter Ling August 18, 2009 / 6:44 am

    Great post Chris, you made me try and set up Exchange on Mail.app again! Question: If I can get it to receive email does that mean IMAP is enabled? I just can’t get the SMTP server to work! My company also has that domain\username deal, and I tried the Password Option to no avail :’(

    • Chris Poteet September 4, 2009 / 12:45 am

      Peter: I’m sorry I’m just now getting to this. Yes, if you can’t get IMAP then it hasn’t been set up. However, Snow Leopard is out, and it’s awesome!

  7. Aram August 31, 2009 / 10:34 am

    Use DavMail (http://davmail.sourceforge.net/). It will allow you to integrate Mac with Exchange. Or upgrage to Snow Leopard.

    • Chris Poteet September 4, 2009 / 12:43 am

      @Aram: I just got Snow Leopard, and I am very happy!

  8. gianluca September 6, 2009 / 9:33 am

    Chris: are you able to connect to exchange 2003 in snow leopard and use mail, ical and address book without problems?

  9. Aram September 6, 2009 / 3:35 pm

    2 gianluca: Snow Leopard won’t support Exchange 2003. For that use DavMail. It is free and is pretty stable. I used it before upgrading to Snow Leopard first with Exchange 2003, and then with Exchange 2007.

  10. Chris Poteet September 6, 2009 / 5:12 pm

    I have all 2007 servers at work, but it won’t work with 2003.

  11. Iaax Page March 11, 2011 / 9:55 pm

    I found myself under the need to configure a friend email address using Exchange and it was a pain in the ass cause new mac books have no support for exchange 2003. So i googled and googles until today when I used bing who led me to your blog. And voila, the problem is solved thanks to davmail and you. :D

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