Will Microsoft Outlook ever get any better?

Microsoft Outlook is bad. Astoundingly bad. Horrendously bad. It’s roughly as bad as an an app can be and still have basic function. It’s probably going to get a little better soon, but I’m willing to bet it’s still going to be a big, bad, bloated mess. Why? Because it does too much, and it doesn’t do it very well.

The history of Microsoft’s bad apps

Microsoft has never done email very well. I think the first time I used Outlook was in 1997, and I have to admit it was pretty decent for the low expectations of the day. It was actually a benefit that it integrated a calendar and email client all in one because it let you create appointments with people attached. That was a big improvement over using paper-based systems or even the other e-mail clients of the time. Unfortunately Microsoft took that early win and learned the wrong thing from it.

Initially Microsoft gave Outlook away for free. It was their way of getting people interested in the internet. However, by the early part of this century they decided there was a “better” way. Microsoft called their desktop client “Outlook Express,” but it had no interoperability with Outlook.

Then, they created a completely different suite of apps, called Windows Live, which were given away for free. In some cases Windows Live Mail was better than Outlook, in some ways it was worse. It didn’t crash as much, because there wasn’t as much function.

Windows Live was killed off and replaced by extremely stripped down versions of a mail and calendar app native to Windows 8 and beyond. These apps were so useless that people well, didn’t use them. They just went to the webmail versions on their computers, and mostly just used their phones for email. It’s pretty bad when one of the world’s leading software companies drives you away from their app because it’s so messed up.

Replacing e-mail with collaboration

In recent years, Outlook has become more of a collaboration hub, whether we like it or not. It freely syncs up with OneNote, OneDrive, and Teams so you can share stuff and create meetings with online collaboration. That should be a good thing, but of course it also creates just another layer of mess on the screen that you have to look at. There’s been some increase in stability, and the configuration process is a little better than it was. But let’s not kid ourselves, it’s still pretty bad.

“One Outlook”

The next goal is to get rid of all the largely ignored desktop apps and replace them with “One Outlook” that supposedly will be provided for everyone and will work the same for everyone. Except, Microsoft really didn’t do that with Teams, did they? Sure, they integrated something called “Teams” onto Windows 11, but the work/school version of Teams is a completely separate app. It’s still two different programs, they’re just named the same because we can’t have nice things in this world. I’m guessing that’s how “One Outlook” will be, and it will really be “Two Outlooks.” Not an improvement.

An embarrassing list

Here’s a list of the things that Microsoft should be embarrassed about. It’s all the things that other email clients and apps do, that Outlook doesn’t. And I’d like to point out, they could have built the app to do any of these things any time they want. But they didn’t. Specifically:

  • Show you how many unread emails you have in the taskbar
  • Actually notice when you’ve read emails on another device
  • Effectively clean offline storage so it doesn’t take up massive space on your device
  • Allow a hybrid mail/calendar view (it looks like “One Outlook” might do this)
  • Integrate iCloud without a third-party plugin
  • Allow you to make changes to a Google Calendar
  • Automatically quiet notifications if it sees you’re in a meeting
  • Use the latest version of the OAuth framework for adding additional email accounts
  • Have a unified inbox that shows you all the messages in your accounts
  • Show only unread messages
  • Allow for a “VIP” inbox
  • Allow you to remove an Exchange/365 account without having to recreate everything else
  • Let you easily rename an account without going 3 menus deep

I could go on and on. Microsoft could really create something killer here, but they haven’t. And chances are, they won’t.

Past disappointment

I’m way past being disappointed with Outlook. I wish someone would really fix it but I doubt they will. It’s going to keep getting more bloated and less useful until it takes over your entire life and kills PCs altogether. Don’t agree? Leave a comment below and change my mind.

About the Author

Stuart Sweet
Stuart Sweet is the editor-in-chief of The Solid Signal Blog and a "master plumber" at Signal Group, LLC. He is the author of over 10,000 articles and longform tutorials including many posted here. Reach him by clicking on "Contact the Editor" at the bottom of this page.