Dec 31, 2022Liked by Steven Sinofsky

As someone who joined Outlook v1 (Ren) and stayed through shipping Outlook 2003, this entry definitely hit home for me. So many shifts, strategy taxes, competing mail clients, etc. over the years. I felt like the last Seinfeld episode of “Going out on top!”

One of my favorite things we worked on in Outlook 2003 was cached mode and specifically the “Walking Around with Outlook” feature. Since WiFi was always spotty and cached mode was new, we would all go down to Crossroads mall with out laptops. They had recently added WiFi so we would all walk around the mall eat lunch and test out how well the feature worked constantly going offline then back online, dropping WiFi, etc.

The other thing I remember was how well Will Kennedy ran the triage room. Any time a developer would bring a bug, they would inadvertently start describing the technical fix. Will always stopped them mid sentence and asked “User boots Outlook and then what?” He would force the Devs to describe the actual user problem that happened before talking tech. He must have uttered that phrase 100 times but finally it became a habit. It was a great technique that I’ve used for years when going through bugs on other projects.

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I agree, Office 2003 was a momentous milestone. I have somewhat different recollections of Outlook though. I always used Outlook off-line, starting with the original beta, and synced mail when I wanted to (usually over POP/SMTP). I was always happy to have my local .PST files (even though Windows Home Server could not back them up, OneDrive does now). I also got rid of the toast. I did not want my life ruled by "you have mail." (I work Twitter the same way, via an Outlook plug-in.) I only dealt with Exchange for a short time with an Office 365 Business account. That reliance on Exchange and Sharepoint was not attractive for me. Of course, none of this is about enterprise perspective.

There has been recent degradation in how mail accounts can be managed and, worse for me, white listing has failed for several years now. Shared calendars are sometimes iffy too, ours being via @msn.com addresses still :). My sense is that alternatives remain worse for consumer and small-business purposes.

Fixing things that are not broken is rampant. I was disappointed when my @msn.com account started fetching automatically, but it is easy to ignore that until I want to catch up on mail, the first stage being screening junk mail whether or not in a junk folder.

It is startling to hear of friends at Microsoft abandoning Outlook after one new Office release or another. Escape seems to be to Gmail (although I have any @gmail.com addresses forward to my hosting-service email address and thence to Outlook). Shared scheduling is also damaged somehow, something I learn when someone sends me such an appointment.

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A big challenge we faced was that the primary mission and goal of Outlook was as an Exchange client. This in particular meant that much of Outlook's value came not only from mail, but mail in combination with scheduling, contacts, and other features (tasks, notes, automation, etc).

There was a promise put out there by the designers of Exchange that the "provider" architecture enabled connectivity to different types of mail (which they did in order to originally support alternate backends). Those protocols (like msn.com, IMAP, etc.) never had the breadth of support to deliver on Outlook on the whole v. just mail delivery. For example, Outlook seamlessly made it so you could have mail on msn.com and contact/calendar/distribution lists in Outlook, but the latter were not part of your MSN account so only existed on one PC (same for using IMAP) as you note. Backing up PSTs was always a nightmare (essentially backing up a live database). As was using the old dialup "always offline" support for anyone but the most technical users.

It was a false promise and we needed to be careful about that. Also with all of this we need to separate out people who were trying everything to make it work and regular people who were not going to try many approaches out, which was most people.

Whether Exchange was not interesting to you as an individual was another difficulty in the strategy. Hailstorm was supposed to be the consumer backend that would deliver a service covering all the Outlook+Exchange scenarios but scaled for the consumer world. That delayed getting many of those features into Hotmail (so did gmail's large storage architecture) so we did not have consumer calendaring until about 2008 with Live Calendar (now Outlook.com).

Today everything finally works :-)

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Yes, I used the calendar and tasks from the beginning and the support for multiple mail accounts is also great. Sharing via msn.com (basically outlook.com) works too and multiple calendars are great. Forms and such were not something I had any use for. I fear there is now some bit rot and a bit of making things simpler than possible.

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