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."

Sug...