Entourage: A journey to becoming an Office application

It’s not often that a new Office application is born. That’s especially true on the Mac. This is a story about Entourage, a product that was called Alpaca for the longest time.

I joined Microsoft in January 1999. At the time, the team I joined was publicly working on Outlook Express 4, 5 and secretly building a Personal Information Manager for Mac Office. When we started the project we shared very little to no Office code. Over a 2 year period we morphed into a product that shipped in the Office box. The first thing I got to do when I joined was basically run the Outlook Express 5 project. I was 22 years old. Can you imagine showing up at a Company and being given responsibility like this? It was just unbelievably exciting (coincidentally, my soon to be roommate, Jimmy Grewal, was given similar responsibility on Internet Explorer). Two 22 year old punks who never shipped anything in their lives shipping what became the most popular browser and mail client on the Macintosh. I remember going over to Apple for meetings some times and they would be like, are you kidding? Where are your parents?

Outlook Express was actually a new name for a product that was called Internet Mail & News. No offense to the people who worked on this, but compared to the competition, IMN was a crappy mail product. Microsoft hired a lot of people from Claris and Apple who helped take the IMN code and build OE. Development and features were added at warp speed. However, the group building Outlook Express and IE were folded into the MacBU about 6 months before I joined. At that point OE was viewed as a product that would grow to become the PIM for Mac Office. Since Windows Office had Outlook, we needed something similar on the Mac. At the time there wasn’t a viable product that offered all the functionality of Outlook in a single application. So when I joined we were all really working on Entourage 2001. At the time, we managed to convince upper management (mainly Ben Waldman, our General Manager and Kevin Browne, our Lead Product Planner and soon to be General Manager) that we needed to do another release of OE to stay competitive and compliment IE 5. It really wasn’t until MacBU took on our group that OE was given any attention. Before that, IE was the sexy product and the one that got most of the attention and resources. Office changed all that.

I remember sitting in a room with a bunch of people and trying to convince Ben Waldman that OE 5 was a good idea (this ultimately meant sucking resources away from Office, the big money maker, for a free product). Somehow we were successful, but I remember being scared to death. So the OE 5 project was born and I got to pick the code name [update: corrected mistake per this post from my first manager]. We called it Newman, after the mail delivery man on Seinfeld. He was famous for saying “When you deliver the mail, you control Information”. The code name for Entourage was harder to select. We had some bad ones, but finally, Jud Spencer settled on Alpaca. If you have ever flown Alaska Airlines you’ll note the Alpaca ads that they have in there. “Alpacas, the huggable investment”. If you watch CNN late at night you’ll also see the commercials. Alpaca would remain the code name and the actual product name till months before RTM… finding a name that no one else was using was next to impossible (remember, dotCom days).

Anyway, OE & Entourage were native Mac applications (no ported code, and no Office code), and we didn’t really follow the methodologies that the rest of Office followed. Entourage, OE and IE were developed in North San Jose, while the rest of MacBU was in Redmond (PowerPoint was in Cupertino). None of us had any exposure to the long established processes of the rest of the business unit, and we all got a crash course.

In addition to being a kick ass mail product we also had to build a calendar, contacts, tasks and notes interface, support internet RFCs like iCal, vCard, and create a data store for all this data. We also had to interoperate with numerous different products (wire protocols, authentication, meeting requests, e-mail formatting etc). On top of that we had to have some features that leveraged the fact that we were an Office suite, and of course we had to “Look and Feel” like an Office application.

That final sentence was the source of so much contention, especially for me. Remember, we were a native Macintosh application. Office still had a lot of legacy code, non native Mac UI, and other things. So “Look and Feel” like an Office application sometimes meant look and feel less like a Macintosh application. Let me give you some examples.


In Outlook Express 5 we wanted to have a fresh and pretty look and feel. I went out and hired the Icon Factory to design about 120 icons from scratch. These were 256 color icons, a big deal in that day. The Icon Factory OE 5 page states: “The goal of the project was to give the entire OE icon suite a cleaner, more “mac-like” look and feel.” By comparison Mac Office and Win Office were limited to 16 colors. And they were the most saturated and ugly 16 colors on the planet. We were “told” that we would have to take our beautiful 256 color icons and make them only 16 colors. Ack! That was battle number one. I tried to convince Office to move their toolbars to 256 colors but it was deemed too expensive. Ack! I panicked. In the end we managed to change the 16 colors to a more muted and pleasant 16 colors, redid most of the Mac Office icons in these new 16 colors and updated the Entourage icons to use the same palate but we could keep our 256 colors.


Mac program had their preferences menu in the Edit menu. Office programs have their Preferences menu in the Tools menu. Guess where OE and Entourage had theirs? One of my favorite accomplishments was getting all the rest of Office to do things like a proper Mac application ;-).


Outlook Express and Entourage had docked toolbars while Word, Excel, PowerPoint had global toolbars. Our toolbars were contextual (they changed depending on where you were in the application) where the others were always global and static. We were told to change our toolbar to be more like Office. Well, that was another long battle that we thankfully compromised on by promising to at least make our toolbars look like Office. However, since we didn’t’ share any code with Office we had to write our own implementation. For Office X we ended up throwing this all away when our new Toolbar implementation for Office (to support 32 bit icons) was done.

Spell Checking, Autocorrect etc.

There are many features that are just expected of an Office application. Two of those are spell checking and autocorrect. These were enormously complex things to do. Our application was built on a Macintosh development framework called PowerPlant. Meanwhile Office had its own custom framework and a lot of work was done on both sides to factor our applications such that we could use Office components without the massive overhead of supporting the office framework in its entirety. This was really hard stuff to get right, but when we did it was just so cool to have the red squiggly. We never did grammar checking.

Shared Features

There were lots of ideas for shared features. Some of them never saw the light of day, and others took a very long time to get right. One of these was the Word/Entourage integration. The idea being that you can access the Entourage address book from Word for composing letters, inserting contacts and customizing Word templates based on your personal information (we created the notion of a “Me” contact in Entourage, that allowed us to do some cool things like auto fill personal information in Word templates, or get driving directions to and from people’s work and home addresses via Expedia). This work required a lot of collaboration between to teams that sat many miles away and didn’t always see eye to eye. In the end the feature worked, and worked well, but it was another one of those amazing learning experiences. There were many more of these shared features. They all required extensive work on both ends. We were really building the bridges between Entourage and the rest of Office that would then be used for many years to deliver much more advanced and user centric features that really leverage the entire Office suite (Project Center in Office 2004 is a good example).

Anyway, our team learned a lot in becoming not just an Office app, but in becoming a team and an integral part of the success of the suite. For the next project, Office X, Entourage was the first application to get Carbonized. Because we didn’t share much code with Office, and because we were the youngest code base it only took a few months to get us running on X. It took many more months to make our Look and Feel stunning on OS X and the good news was that the rest of Office really had to purge a lot of the old crust to get to X. Since X was all about a new Look and Feel called Aqua, this was a boon for us, and it meant that all of Office got 32 bit icons. A far cry from the 256 colors in 2001! We also got more and more Office functionality as a result and that was great. Entourage really started to become the hub of Office, and that is so very true in this year’s release.

Comments (13)

  1. Thank you for this post. I enjoyed the backround information. I subscribe to TidBITS Talk and always make a point to read your posts. They are part of the great balance in the community there.

    I have moved to Entourage as a PIM for my Treo. I used Claris Organizer/Palm Desktop from its first month of release. Entourage is clearly developing while P. Desktop is not. I don’t know that I will every switch from Eudora to Entourage. Too many years of use and the email database in Entourage feels to big and seems to need more maintenance than Eudora. Maybe it doesn’t and I just have to try it for a longer time.

    My biggest surprise is that MS Office now runs on UNIX. Who would have thought that ten years ago?

    Thanks again, Tarik

  2. bob says:

    Can you give any insight into why Microsoft still has not released a MAPI native email application to work with the exchange server. The current Entourage implimentation is spotty at best, and usually unworkable. Why has Microsoft dropped the ball, forcing OS X users to use the classic Outlook client?

  3. matthew says:

    I thought Internet Mail & News was pretty good, and not the wormhole-ridden, top-posting HTML spouting, can’t output an internet-friendly email that it is Outlook Express. At least that was my experience on Windows 95, when I used Mail & News

  4. Sam says:

    You can’t compare Mail & News on Windows & Mac as they were totally different animals. The same is true of OE on Mac & PC you were talking about.

  5. Omar Shahine says:

    Bob, I can give insight but that will have to wait for another blog post… it’s a long explanation ;-).

  6. Tim Bo says:

    Very interesting… glad to see some people in MS have taste. IE 5 and Entourage were groundbreaking products on the Mac. At the time they were released, IE 5’s Tasman rendering engine and Entourage’s feature set were really hot stuff.

    I’d be interested in hearing about Jud Spencer’s contributions as I remember seeing his name on Claris Emailer (which was state of the art when it was released).

    I still think Entourage is much nicer than Outlook Express (Windows version), although the OS X port still doesn’t feel totally native yet and it’s really showing it’s age when rendering html or doing searches.

    From what I’ve seen Entourage 2004 seems like a relatively minor upgrade feature set wise for me although the horizontal layout is probably worth the price of admission. I also have my fingers crossed that the code is now polished, optimized, and speedy on my G5s (Office is my only major app that still feels sluggish). My wish for entourage is that it could sync and play nice with apple’s overlapping built in apps (mainly address book and iCal) in some semi-automatic way as well as take advantage of iPhoto.

    It’s funny that so much thought went into those icons. While they are light years better than ugly dayglow office icons, they have always stuck out for me as being kind of ugly and are one of the first things I go in and replace! At least they are easy to get at.

    I’m eagerly awaiting VPC that runs fast and clean on the G5! Good luck.

  7. James Rhodes says:

    Like the last poster I agree that Entourage was state of the art when it was released. Until recently I felt it was by far the best mail client on any platform. I also remember feeling that it had some Emailer DNA and would be interested in hearing about people from the Emailer team who worked on Entourage.

    I’d also be interesting in hearing about how Entourage renders html. Do you guys use webcore?

    Lately the program has stagnated. I got a chance to look at Office 2004 at Macworld and was disappointed that changes seemed to be minor and incremental. I definitely would not upgrade unless my employer pays for it. Entourage and Word are almost always open on my computer, but I don’t see much new in either of these programs… Notes and projects will not be something I will ever use… What I care about are the basics, searching, sorting, editing, filing, HI/UI.

    This said:

    **Stuff I like in Entourage 2004:

    -I like the preview on the right (works like a psuedo column view)… in fact I wish it looked more like column view.

    -Exchange support

    -Live filtering is now live (don’t have to press return)

    **Stuff I don’t like in Entourage 2004:

    -The way SMTP servers are handled is still annoying. When you are moving around you often don’t need to change POP settings but you need to do a single global SMTP change. Mail.app makes this easy. Entourage still does not.

    -If you use preview to the right, items in the inbox are now 2 lines even if you have a huge screen with tons of horizontal space…. My preference would be to see all the info on one line or to be able to truncate the info in columns.

    Mail.app does a much nicer job of handling viewing of multiple mailboxes. With a single click it is very easy to view the mail from a particular mailbox.

    -Export from the contacts or from the calendar is still clumsy. Ideally there would be a simple way to sync the address book and ical.

    -Notification in the dock is still not as good as mail.app.

    **Things I’d like to see in the future.

    -A really great minimized mode where the window is minimized on the desktop and you have good feedback about new messages coming in. A single click would open up the window full sized.

    -Google-like prioritized indexing.

    -I have am now used to moving around and editing my toolbars. It’s ironic that Entourage is still lacking this feature as it was pioneered Office and the OS X implementation seems to have been cribbed from MS’s Explorer 5 for OS 9. I never use many of the icons (reply all, print, link, move, categories, and so on and would like to reduce my screen clutter by removing them).

    -The live search box should use the standard OS X icons. The program icons should be more maclike (right now they are sort of an odd Windows/OS 9 amalgam).

    -Icons in general should be more Maclike…

    -Preferences should be consolidated.

    Anyway you get the picture. Despite these gripes, I have a great deal of respect for the Mac BU. You guys have put out lots of great innovative software in the past, and I hope you will continue to in the future.

  8. Omar Shahine says:

    James, thanks for the comments. I’ll forward these on to the Lead Program Manager for Entourage.

  9. David Gonzales says:

    Thanks for the great post. I’ve been a fan of the Mac BU ever since it was revamped in the Office 98 era… People like yourself and Jimmy Grewal have provided interesting glimpses into it’s inner workings. More more!

  10. "<i>it was just so cool to have the red squiggly. We never did grammar checking.</i>" <!– please forgive the HTML, i don’t know if this blog deals with it… –>

    i always have entourage open, so i do a lot of my writing in it rather than waiting for Word to boot. when ever i’m writing something important, i’ll go ahead and wait for word to boot, <i>only</i> for the live grammar checker. if Entourage had this, i probably wouldn’t have a need for word any more, aside from opening files from other people. does this debut in entourage 2004, or will i have to continue to wait for word to boot?

    <i>At the time they were released, IE 5’s Tasman rendering engine and Entourage’s feature set were really hot stuff. </i>

    is it just me or does Entourage X still use the IE 4.5 rendering engine? any change in 2004? Tasman, WebKit, or IE 4.5?

  11. Omar Shahine says:

    Entourage X uses the IE 5 rendering engine. Entourage 2004 uses Tasman (same as the MSN client). We are looking at WebKit for a future version.

  12. eddy kestemont says:

    nice and interesting post!

    BTW is it me or Entourage? Can’t get customization of such bit of information like ToDay color in Month calendar view (the salmon pink is nearly invisible on a Imac G4 screen).