Outlook is a Mess (Premium)

Microsoft’s haphazard way of updating Outlook across its many supported platforms is undermining the product. This month’s announcement about new Outlook features nicely showcases the problem.

And I almost missed it, too. These updates were somewhat lost in this month’s mammoth list of improvements across Microsoft 365. But Outlook is picking up some much-needed updates on Windows, Mac, Android, iOS, and web, too. These updates are notable for a number of reasons, and they represent the first major changes to the product this year.

And it’s a fricking mess.

Outlook is a bit of a sore spot for me: Microsoft maintains multiple versions of the product across many platforms and there is precious little consistency between them. When the software giant purchased Accompli in 2014 and then announced that it would it would transition that app to become its new version of Outlook on mobile, I had hoped that it would also consolidate the look and feel and functionality of all of its Outlook clients.

That hasn’t happened. And if you look at products like Outlook 2016 on Windows or Mac, (Outlook) Mail on Windows 10, Outlook on Android and iOS, Outlook.com (consumer), Outlook on the web (Office 365 commercial), and probably some others I’ve missed, you will immediately notice that they are utterly inconsistent with each other. But that’s just the UX: Less obvious is that these products often don’t work like each other, or even offer the same features.

And when former Acompli CEO Javier Soltero, who had been leading Microsoft’s Outlook efforts since the acquisition, moved into a new position running Cortana back in March, I worried that Outlook’s evolution would move even more slowly. That maybe Microsoft had simply stopped trying.

This month’s improvements don’t hint at any grand consistency consolidation, sadly. But they’re also not a response to Google’s recent and long-overdue Gmail updates either. Instead, these changes parallel what’s happening at Gmail, since they are likewise long overdue. And as is too often the case with Outlook, that some of these features were not already in Outlook is rather astounding. (Multiple time zone support? Really?)

And consistency is still very much a problem. Perhaps the problem. As you will see, these new features are rolling out in a patchwork way across seemingly random Outlook versions. As has long been the case with Office 365 updates in general, tracking what works where is difficult. As is the timing of when features appear where.

Anyway, here’s the list, and accurate as I can make it.

Bill reminders in Calendar in Outlook.com. The web version of Outlook.com will now help you automatically track bill payments. “Outlook will identify bills you receive in email, show you a summary at the top, and automatically add a calendar event on the due date,” Microsoft notes. “You will also receive an email reminder two days before the due date so you can always pay your bills on time.”

Suggested event locations and meeting rooms in Outlook for iOS and Outlook 2016 for Windows. Outlook for iOS can help you find free meeting rooms and other locations for events. This works both within corporations and in public locations. This feature is “coming soon” to Outlook for Windows.

Meeting RSVP tracking and forwarding in Outlook 2016 for Windows and Outlook on the web. Outlook will “soon” let you track responses and RSVPs for the meetings you create, on Windows and on the web (Office 365 commercial).

Support for multiple time zones in Outlook 2016 for Windows and Mac. I first complained about this functionality in the late 1990s. Yes, seriously. But Outlook will finally let you configure the start and end times of appointments and meetings across different time zones. On Windows and Mac at least.

Show organization directory details in Outlook for iOS. The details of your organization’s Azure AD-based directory is now added to your Outlook contact information, on iOS at least.

BCC warning in Outlook 2016 for Windows. Outlook will now warn you when you’ve been BCC’d in an email message so you can decide whether to reply or reply to all.

Draft folder sync (multiple platforms). The ability to sync your draft email folders across devices is now available in Outlook across Windows, Mac, and Android, and it is coming this month to Outlook for iOS.

Office Lens in Outlook for Android. Integrated Office Lens scanning technology is now available in Outlook for Android and is coming soon to iOS.

Quick reply in Outlook for iOS. Outlook picks up Quick reply on iOS, but this feature is also coming to Outlook for Android this month and then to Outlook 2016 for Mac “later this summer.”

Favorite people in Outlook for iOS and Android. In June, Microsoft will enable a feature that helps Outlook users tag their favorite people and keep them “front and center in your mobile search experience.”

Office 365 meeting events in Outlook for iOS. Starting in June, Outlook for iOS will support the ability to track events in a group’s contact card.

Block external content in Outlook for Android. Sometime this month, Outlook for Android will finally pick up the ability to automatically block external content in email messages.

Single Office 365 account in Outlook for Android and iOS. Answering a key concern of IT, businesses will be able to prevent users from commingling corporate and personal accounts in Outlook on Android and iOS. This starts in June.

What a mess.

As is the case with Windows 10, I’d love to see Microsoft take a step back here and just work to make these products more consistent with each other. Functionally, and from a UX perspective.