The Microsoft news train hasn’t stopped over the past week, but I’m about to take some time off. Notepad will return in three weeks’ time, just before Microsoft’s big Ignite conference. As always, you can get in touch with me at notepad@theverge.com if you have any questions or tips about what Microsoft is up to.

Also this week: Microsoft wants you to talk to your PC and have AI control it, the first “Xbox” handhelds aren’t shipping full baked, and Mico is here to replace Clippy.

Outlook users have only just got over the webification of Microsoft’s email client in recent years, and already there are major changes on the horizon. Sources familiar with Microsoft's plans tell me that the company recently reorganized its Outlook team under new leadership with a focus on rebuilding the email client for the AI era.

“Instead of bolting AI onto legacy experiences, we have the chance to reimagine Outlook from the ground up,” Gaurav Sareen, corporate vice president of global experiences and platform at Microsoft, writes in an internal memo seen by Notepad.

Sareen is now taking over direct leadership of the Outlook team from Lynn Ayres, who is taking a sabbatical from Microsoft. He lays out a somewhat unclear vision of how Microsoft is going to transform its email client into more of an assistant, in a way that sounds very much like what Copilot already aspires to be.

“Think of Outlook as your body double, there for you, so work feels less overwhelming and more doable because you are not facing it alone,” Sareen writes in his memo. “With Copilot, this body double becomes even more powerful. Copilot turns Outlook from a set of tools into a partner that acts.”

Sareen envisions a future version of Outlook where the email client reads your messages, drafts replies, and organizes all of your time. That type of overhaul will require some changes to the way the Outlook team is organized and a renewed focus on shipping even faster. Sareen is expecting weekly feature experiments, rather than quarterly ones, and “prototyping and testing in days, not months.”

This also means that AI will be embedded in how Microsoft designs Outlook, builds it, and then ships it to consumers and businesses. “AI will not just be in our product, it will define our culture, helping us move at the speed this moment demands,” Sareen says.

The pressure is now on the Outlook team to build and deliver some type of AI overhaul to an email client that’s used by millions. Microsoft’s last major revamp to Outlook started a few years ago, with a web-based “One Outlook” email client that’s replacing its Windows, Mac, and web versions of Outlook. Microsoft has struggled to perfect it in recent years and bring it up to the standard of the existing desktop apps it’s trying to replace.

Sareen now wants Outlook employees to find “courage” to “let go of old ways of working” and “step forward when the easier path is to wait.” One Outlook was a big challenge for Microsoft, and attempting to transform an email client that Microsoft’s most important customers count on with unproven AI features is going to be an even bigger task. Executives at businesses around the world rely on their Outlook calendar every day, and Microsoft will have to tread carefully with AI features that could upend an important work tool.

The upcoming changes to Outlook are part of ongoing reorgs across Microsoft that are almost always about AI. Microsoft’s LinkedIn CEO, Ryan Roslansky, took on an expanded role as its head of Office earlier this year in an AI shake-up. Sareen reports to Roslansky, who leads all of the Office, Outlook, and the Microsoft 365 Copilot app teams.

The challenge for both Roslansky and Sareen is to convince Microsoft’s own employees that rebuilding Outlook for AI is the right thing to do. I’ve spoken to plenty of Microsoft employees who are unconvinced by Microsoft’s AI efforts and the investments being made. That’s not stopping Microsoft’s Outlook leadership from dreaming big, though.

“Next year, every product will claim to be AI native,” Sareen writes. “But there will be teams that just slap AI on products and make buzzword complaint claims. And there will be teams that will have actually rebuilt their product and culture from the ground up to make that real. I am betting my leadership that we will be that team.”

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