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

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.