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Microsoft is killing one of its biggest apps. And replacing it with something… users didn't ask for. Outlook has over 400 million active users. Except, there are two separate Outlook apps? And three mail apps. But Microsoft wanted everyone using the new Outlook. Simpler, fewer features, and packed with AI. This is how Microsoft killed one of its biggest apps, and… what's hiding inside the New Outlook. So why did Microsoft kill one of the most popular apps on Windows? All of this started on May 22nd. In 2022, Microsoft released an early preview for the new "Outlook for Windows". And almost immediately, people were furious. So, why?
Outlook Classic is what most people were used to. It's a more traditional, built-in email app with keyboard shortcuts, custom toolbars, rule management, it's highly customizable. A lot of people use this version, especially at work. But there's also another, potentially bigger app. Windows Mail. It's the simple app pre-installed on Windows, and… people really loved this app. It integrates with other Windows apps like Calendar and People, it has a clean, simple UI, and it can have multiple emails in one inbox.
It was straight to the point, which for Microsoft, is unusually good. But now, with Microsoft's new update, there were two versions of Outlook. Old Outlook, New Outlook, and also: Windows Mail. Three Microsoft mailing apps. Very confusing. So what was new? It turns out… a lot. Much of which was unwelcome. But let's start with the surface changes. First, a UI overhaul. At its core, it still combines email, calendar, and a to-do list. But Microsoft added features like Loop components, which let teams collaborate in real time, directly inside emails.
You can pin emails and snooze them. They overhauled categories, and you could have multiple Outlook accounts as well as Hotmail, Gmail, Yahoo, iCloud, and more. There was tighter integration with 365 apps, especially Teams and OneDrive. And, of course, this wouldn't be a modern tech update without AI. The new Outlook was heavily integrated with CoPilot. Summarize emails, organize your inbox, draft emails, prepare for meetings, manage your calendar - Microsoft was integrating CoPilot into all parts of Outlook.
"Copilot is a powerful tool that can help you save time, achieve more, and stay on top of your inbox." It seemed, on the surface, like a new, fresh, consolidated email client. So, why was everyone so upset? Well, for two reasons. The first came in June 2023, when Microsoft announced that this new Outlook would replace Mail and Calendar the following year. That's right. Mail and Calendar were being shut down. And of course, the new default mail app on Windows 11 would be "new" Outlook. Used Mail for years? Or potentially a decade? Too bad. Time to use New Outlook. People were furious. "I hate this so much. The old Mail and Calendar apps were simple and functional,
while the new Outlook is complete garbage by comparison - and that's before you get into some of the more seedy aspects of the app." "They'll have to take the Outlook desktop app out of my cold dead hands." But there's more. By August 2024, Microsoft formally described the new Outlook for Windows as ready for commercial customers. Enterprise users would also be forced into the new Outlook by April 2026, with the ability to opt out until then. "Windows 10 was perfect with its apps for contacts, mail and calendar. Calendar and tasks seen in notifications. Everything was taken from us in W11." So. why do this? Why does Microsoft want to push everyone to another
mail app? Millions are already using Windows Mail, or old Outlook, so… why? Well, that is the second reason people are annoyed. There were a lot of other changes to this new Outlook. CoPilot was just the beginning. The deeper people looked, the more annoyed they got. A lot of people, especially in programming or research, are using multiple LLMs, since, they're all good at different things. But, that can get pretty expensive.
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Stay at the cutting edge of AI without the lock in. Click the url in the description and try Mammouth today. Thank you to Mammouth for sponsoring our videos. From Microsoft's perspective, all of this was a bit of a mess. Microsoft said "It's our intention that every person be able to access all of their emails - in one spot - on any Windows 10 or Windows 11 device". They wanted things more… "streamlined". For years, Outlook existed in multiple versions, each designed differently for web, desktop, and other platforms.
The new version simplifies that. It runs on a single codebase, designed to work across every system. That makes updates easier. Faster. More consistent. They said "Now everyone with Windows gets the best of Outlook built into Windows for free. You will write better emails with advanced AI built into the new Outlook for Windows to help you write impactful, clearer, mistake-free messages." "Best of Outlook" being quite subjective there. Because that came with some changes. They said it was "designed to bring consistency across our Windows and web codebases". So… the New Outlook… was essentially a website with a wrapper.
"I tried it for like 5 minutes and wanted my full paid-for Outlook client back. I have 4 methods in place to block this crappy web version. Just wait, they are forcing everything into Teams as a be-all communications tool." And this meant that things people expected weren't there. And some things people didn't want, were. The old Outlook allowed users to access emails without an internet connection. The new one? Not so much. Apparently, this was "coming soon"… whatever that meant. And this created another problem. PST files, used as local storage for emails offline, stopped working properly.
For many users and small businesses, that meant losing access to years of archived data. Then there were enterprise tools. Plugins like VSTO, COM add-ins, and customer management integrations - tools businesses rely on every day - were either broken or missing. And it didn't stop there. Basic app functions started failing. Search folders vanished. You couldn't hyperlink to local files. The File menu changed or went missing entirely. Drag-and-drop didn't work the same. Mail merge features were gone. This was just… worse Outlook. There's a big reason for all this.
The new Outlook was a web-based wrapper. Not a native app like Mail or Calendar. Many people did give it a genuine go (show top comment), but the UI… was just a bit unfinished. People also noticed something else in the UI. Ads. To be clear: free Outlook always had ads. Banner ads, to be specific. But now, Microsoft just went and put these in your inbox. These aren't like sponsored emails. Clicking them just takes you to an external page, like a banner ad. Even some paid users were seeing these. But even that wasn't the biggest issue. The real change was happening in the background.
The new Outlook is cloud-based. And not everyone was comfortable with that. "The new Outlook is a Trojan horse. I don't think most people realize that Outlook will grab their emails, account details, passwords, calendars and contacts, and upload them to Microsoft's own servers. It turns something you own and control into something you simply rent. And it's your own data!" "I am so mad. I just bought a new computer and the Office Home 2024 package. I am now stuck with that godawful new Outlook. It's clunky and unresponsive." Complaints flooded everywhere. And if people weren't complaining, they were looking for tech tips to opt out of the update.
Guides started popping up showing users how to bypass or disable the new Outlook entirely. It was all too much. People were sharing and migrating to other email products. So, what did Microsoft do? Funny how many deep dives we've done on email platforms (Show). But if you actually care about this sort of stuff, subscribe! It helps us a lot. Thank you. Setup The enterprise rollout was moved back to March 2027, giving businesses more time to opt out. And support for old Outlook was pushed even further.
"Existing installations of classic Outlook through perpetual and subscription licensing will continue to be supported until at least 2029." Since these customers directly pay for Outlook and 365, their voice was definitely the loudest - although I wouldn't call it a victory. But for fans of Mail and Calendar, the story doesn't have a happy ending: Tension Mail and Calendar were nuked, just as Microsoft intended. If you open Mail now, you'll see this popup. In February 2025, Microsoft started automatically installing the new Outlook app on Windows 10 PCs
via security updates if it wasn't already present, further pushing users off Mail and Calendar. Many users, though, had already left. Complaints continued to pile in. "Anyone else hate the New Desktop Outlook?" "I am so mad. I just bought a new computer and the Office Home 2024 package. I am now stuck with that godawful new Outlook. It is clunky and unresponsive." Even by 2025 and 2026, basic features were still being added - features that older apps already had. And it raises a bigger question. Does it feel like Windows itself is getting worse?
The operating system now feels more like a platform for promotion. The Windows 11 Start menu includes "Microsoft Store app recommendations". A space that used to be purely functional… now doubles as advertising. Key features get removed, the backlash follows, and then those same features return as "innovation." One example is the removal of the classic "never combine taskbar buttons and show labels" feature. Then, Microsoft announces: "We're excited to bring you an early version of one of our most requested features for Windows 11, never combined mode." And now, the same pattern seems to be repeating with Outlook.
Search is slower. Tasks take longer. Basic functions feel harder to use, and features are missing. And then… there's Copilot. For many users, it's just one more layer they didn't ask for. At this point, some people are even starting to miss Windows 10. Having multiple apps for mail was a bit of a mess. But it was a weirdly good mess. Two different mail apps was actually okay. They both serve different customers: regular, personal inboxes, and businesses with 365 Outlook. But Microsoft wanted to put everyone in one app. So they kill off products people actually use, to rebrand everything into things that sound modern and clean. I think there's a bigger problem here.
Products like Outlook are sold to companies, and they're usually not pitched to the everyday people using them. This is the buyer-user split. The person who buys Outlook isn't necessarily the person who has to use it every day. They're pitched to the managers, executives, and heads of IT or other team leads. Bundled with other apps, packages, and ways to improve productivity. They end up not being designed with the day-to-day workers in mind. Though I suppose "Microsoft's customers are the shareholders, not the users."
A lot is actually tied to the stock price, yet something is changing at Microsoft. Investors aren't so thrilled about all this AI spend anymore. Microsoft's market cap dropped $500 billion in a single week after they announced more AI spend. Click here to learn the rest of the story.
