Microsoft Entourage

» see microsoft.com/mac as it lived, on the wayback machine

~ the obituary ~

entourage was a mac product. macs were not in my orbit in the 2000-2010 window. by '02 my desktop machine in ankara was a beige windows tower running 2000 then xp, the mail program was outlook express then outlook, and the laptops i borrowed at university were also windows. macs were rare in turkey then for cost reasons more than anything else. i first sat in front of an os x machine in maybe '07 at a friend's apartment, and even that machine was running mail.app rather than entourage. so the program existed in a parallel universe i could read about in macworld translations but never actually open.

microsoft shipped entourage in october 2000 as the personal-information-manager for office 2001 for mac. it was not a port of outlook. outlook on windows had grown up around mapi and exchange and a code lineage that did not move to classic mac os cleanly, so the macintosh business unit inside microsoft built a separate program that took over the role outlook express had played on mac through the late '90s. it did pop and imap with address book and calendar and tasks and notes built in, all as one program rather than the five-app suite that mail.app plus ical plus address book later became on os x.

the mac bu was an odd internal structure for microsoft. it sat inside the larger office division but answered to a separate manager and shipped on a separate cycle, with its own ui sensibility that was supposed to look at home on mac instead of being a windows port. that is why entourage existed as a brand at all. the windows side of office had outlook, the mac side had a thing that did the same job under a different name with a slightly different feature set. mac users got a mac-feeling email client rather than a windows port that ignored platform conventions.

the limitation that defined entourage for its first eight years was exchange. corporate mac users wanted real exchange support, the kind outlook had on windows, with calendar invites that round-tripped properly and global address lookups that worked. entourage hacked around this with webdav for a while, which was clunky. the web services edition shipped in late '09 with the actual exchange web services protocol on top of the existing entourage codebase, but by then the writing was on the wall.

~ the case file ~

~ how it landed ~

the october 2000 launch was bundled inside office 2001 for mac, the last office version targeting classic mac os 8 and 9 before the os x split. entourage 2001 ran on a mac with at least 32 megabytes of ram and a powerpc processor. for the small but loyal mac base that had survived the apple-near-bankruptcy years of '97-'98, entourage was a meaningful upgrade over the bundled outlook express that had shipped with office 98 for mac.

entourage x in 2001 added os x as a target. entourage 2004 introduced the project center feature that let you group emails and calendar items by ongoing projects, which was a workflow idea that did not exist in outlook on windows at the time. entourage 2008 dropped powerpc-only support and went universal binary for the intel transition. the program kept its identity through all of those releases as the mac-specific office mail app with a name that was not outlook.

~ the slide ~

the cracks were always exchange. corporate mac deployments in the mid-2000s were a niche but a vocal one, and the noise around incomplete exchange support was constant in the mac-it press for years. microsoft's mac bu was small, the engineering bandwidth to keep building a custom exchange client in parallel with outlook on the windows side was limited. the rumor cycle of "outlook for mac is coming" started in maybe '07 and ran for three years before it shipped for real.

the second crack was apple's own mail.app, which had become competent enough by os x leopard in '07 to handle pop and imap and even basic exchange. mail plus ical plus address book plus calendar handled what entourage handled, came free with the machine, and integrated with spotlight in a way entourage did not match for a stretch. for a mac user who did not have to talk to exchange at work, paying for entourage as part of office mainly bought you the project center.

~ what carried over ~

office for mac 2011 shipped october 26 2010 with outlook for mac, ending the entourage brand. outlook for mac was a from-scratch rewrite using a cocoa frontend on top of a modern exchange-web-services backend. it took the entourage user base, kept the database format compatible enough to import, and put the outlook brand back on the mac side of office for the first time in over a decade. entourage 2008 itself got patch updates until march 2013, when version 12.3.6 became the final build for users who had not moved to office 2011.

the legacy of entourage was mostly that microsoft maintained a mac office product at all through the 2000s, when the strategic argument for doing so was thin. the program was the proof that the mac bu could ship a major application on a separate ui culture from the windows office team. that argument carried into the office for mac 2011 and 2016 releases that followed, where outlook for mac kept the mac platform conventions entourage had established.

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