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Microsoft Outlook is Getting an AI Overhaul Under New Leaders (theverge.com) 50

Posted by msmash from the up-next dept.
Microsoft has reorganized its Outlook team under new leadership as part of a broader effort to integrate AI into its core products. Gaurav Sareen, a corporate vice president at the company, recently assumed direct leadership of the Outlook division after Lynn Ayres, who previously ran the team, began a sabbatical. The move represents the latest in a series of AI-focused restructurings across Microsoft's divisions. Sareen wrote in an internal memo that the company now has an opportunity to reimagine Outlook from the ground up rather than add AI features to existing systems, according to The Verge.

Ryan Roslansky, the chief executive of LinkedIn, took on an expanded role earlier this year as head of Office. Sareen now reports to Roslansky, who oversees the Office suite, Outlook and Microsoft 365 Copilot teams. The restructuring comes after Microsoft spent several years developing One Outlook, a web-based version meant to replace separate Windows, Mac, and web applications.
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Microsoft Outlook is Getting an AI Overhaul Under New Leaders

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  • Oh great! (Score:5, Insightful)

    by Going_Digital ( 1485615 ) on Friday October 24, 2025 @12:57PM (#65747958)
    Yet another bug ridden re-build of outlook with AI entrenched with no option to switch it off, enough already!

    • Re: (Score:2)

      by dysmal ( 3361085 )

      We've got Outlook classic, new Outlook, and soon we'll have new new Outlook?

      It's fucking email. Electronic Mail. Treat it as such. If you think you need AI to help you handle that, then there's something very broken and you should probably look in the mirror.

      • Re:Oh great! (Score:4, Interesting)

        by pmsr ( 560617 ) on Friday October 24, 2025 @01:51PM (#65748088)

        It is even sillier than that. At my work, machines cloned from the same image, and after you install Microsoft 365 sometimes you end up with Outlook Classic and Outlook. Sometimes Outlook and Outlook (new). Sometimes both are called Outlook, and we distinguish by the slightly different icon. When they release this Outlook Copilot version it is not going to be fun, not it is not.

        • Try using the web-based one, which some portion of our user base is required to do for $reasons. Every day when you log on it's a new adventure trying to figure out where various buttons and controls and similar have moved to while you were asleep, and which functionality broke in the same time frame.
      • Thank you.

        email is simple....I don't need something to Auto sort or manipulate my incoming or outgoing emails.

        I don't like a fucking web interface...never as clean and snappy as the local app based version.

        I don't need Clippy or Copilot helping me with it....

    • I remember when Microsoft used to innovate and iterate on their existing products. Their UI components were a core part of the operating system and everything was instant fast. Now, anytime someone with enough political capital wants to take a product in a new direction, they're required to build something new rather than improve what exists, and everything is an encapsulated Chrome rendering and has just enough lag to drive someone familiar with "the old times" a little crazy.
    • >> Microsoft has reorganized its Outlook team under new leadership as part of a broader effort to integrate AI into its core products.

      .

      All the more reason to avoid Microsoft apps.

  • they wont do this, but (Score:3)

    by ZERO1ZERO ( 948669 ) on Friday October 24, 2025 @01:00PM (#65747966)
    I can still hope that they decide to make an email client that is actually decent and makes me want to use it. Making it work properly with standard IMAP servers would be a great start.

    Also, last I checked it didn't integrate with your contacts on the Mac, so this meant you had to maintain 2 contact lists if you were a mac user. Absolutely retarded.

    • In my experience with it (I am using it daily, have been since 2021) Outlook (Classic) does not have very good search. Maybe they should nail that down before making it Outlook (Copilot edition)? Just an idea..
  • And they're going to get it because you don't have any alternatives. Microsoft has completely embedded itself in the Enterprise. There isn't anything that can hang without work and active directory.

    And this means every single email you send and receive gets used by Microsoft to train their AI.

    Companies will allow it because they're all owned by the same handful of billionaires and they're all working together on a huge automation project to eliminate most if not all jobs

    Capitalism is failing in

    • Re: (Score:2)

      by sinij ( 911942 )

      And this means every single email you send and receive gets used by Microsoft to train their AI.

      This problem is easily solvable - poison the data.

      • Re: (Score:2)

        by sinij ( 911942 )
        To clarify, this is easily solvable at the enterprise level. All you have to do is feed AI slop back into the system small percentage of the time for the entire dateset to become worthless to train AI. You can also point to point encrypt everything. Plus, there are always lawyers and litigation.

        MS messing with Enterprise is extremely unlikely. Abusing individual home users - sure, I can see them doing that.

      • And this means every single email you send and receive gets used by Microsoft to train their AI.

        This problem is easily solvable - poison the data.

        You could even automate that. I see a business opportunity.

    • What does your therapist think about all this?

  • Years ago email was alright, then MS made Outlook and email sucked. Now they're adding AI, it'll make AI as a concept suck everywhere. This'll be fun!

  • and people keep using it, because that is what they are used to.

    • Re: (Score:2)

      by sconeu ( 64226 )

      and people keep using it, because that is what they are used to.

      And people will keep using it, because that is their standard corporate email client.

      • Re: (Score:2)

        by EvilSS ( 557649 )
        This. Anyone using it for personal email, well, that's on you. But for corporate email, there's not much else out there for stand-alone (non-web) email clients. At least not much worth looking at.
  • I don't want a web-based Outlook to replace my Mac Outlook. I like the fat clients. Replacing everything with a single web-based client sounds terrible.

  • Can't wait; I mean certainly a mail and calendaring solution that has a history of stretching back thru mail & Schedule+, for almost 35 years now should obviously be 'reimagined' after it could not possibly represent one of the more refined and curated products/feature sets or anything.

    I know especially here on Slashdot, people are going to line up to say how much better, is. But the reality is for a full suite of mail, tasks, shared-calendaring, notes, contact management solution; Outlook + Exchange (

    • Re: (Score:2)

      by flippy ( 62353 )
      I will definitely disagree, as you predicted, with your statement "people like Outlook." I'd be much more willing to say "people are familiar with Outlook, and lazy enough to not want to look for an alternative." Outlook is the definition of low-hanging fruit. It comes with the OS, is there already, you don't have to take any extra steps to install it, etc. Especially in a situation where a user is only using it as an email client, it's a bloated pig. But, it's a bloated pig they already have and will put u
  • So.. outlook is mostly used to read, write, and schedule. There isn't much room for 'AI' in there unless you are picturing having an 'assistant' that autonomously replies or schedules for you.. which I imagine being novel until it decides to channel /b and emails erotic poetry to one of your customers, then get switch off by IT policy.

    • Scheduling could be the killer app for AI integration.
      "All hands meeting last friday afternoon? Nope, OutlookAI didn't tell me so I went home at lunch. Dear oh, dear, never mind, what can one do?"

  • So there will be yet another rewrite of Outlook that makes it even worse. Maybe they can make it feel even less like a Windows application than it already does.

  • It's the Microsoft Bob of email clients. MS should be paying people to use it.

    I still miss the last version pre-ribbon, where rules were easy to create, keys could be reassigned and the mail editor was MS Word.

    • Re: (Score:2)

      by gweihir ( 88907 )

      Yep. I would read all my email forwarded to my own servers, but the MicroShit stuff apparently trashes forwarding rules frequently. I could do automated diagnostics (sending test emails), but at some point things are to broken that investing time makes sense.

  • Thought it said Microsoft getting new AI leaders (Score:3)

    by caseih ( 160668 ) on Friday October 24, 2025 @01:43PM (#65748074)

    And I thought, that sounds about right.

  • Disable CoPilot. Useless Clippy bullshit.
  • Outlook has become the catch-all term for poorly designed, poorly executed, feature lacking, functionality lacking email clients. No serious professional would ever use Outlook, it's lacking basic standards, for instance, why can't you see the “reply to” header? It's missing, there is no official way to enable it, except it's a critical header. Why isn't PGP / GPG built in by default? Why does Outlook using a proprietary format? Why does the interface make sure you guess on what you're tryi
    • I can't fully defend Outlook, but I do believe many serious professionals use it, limitations and quirks and all.

      I am curious, though- what email client do you recommend instead of Outlook or other "poorly designed, poorly executed, feature lacking, functionality lacking email clients"? I have been looking, use Thunderbird myself (its basically OK), but I don't see a lot of great stuff in the "email client" space. I'd love to be wrong, though.
      • My problem with Outlook is that it doesn't handle email correctly, objectively. I don't want to use Microsoft email, I want to use email, and that's why Outlook is terrible because at every possible avenue Microsoft will do something to make Outlook functionally handicapped.

        If you would like to know what I'm using on this computer, Betterbird, is it perfect? Nope, but it's email, it's not Mozilla email, or Insert overriding company email, it's just email, and it works just like basic, simple, standard e
        • Thank you, these are good points! I will look at Betterbird, I had not heard of that before. Also, the tendency to make things "Microsoft version" is a terrible habit that company has- examples I can think of from the top of my head include their development of ooxml for MS Office, rather than sticking to the existing ODF. Nominally, MS states that they do things like this for added features (for the doc example [microsoft.com]), but the outcome is reduced interoperability and lock in. I think a similar dynamic exists for

  • Oh. (Score:2)

    by Reygle ( 5392954 )
    Most users: "Okay but that's the 4,371st last straw."

  • Any chance for non-paywalled version of article? (Score:3)

    by blahbooboo2 ( 602610 ) on Friday October 24, 2025 @02:43PM (#65748238)

    Whats the point of posting an article no one can read if theyre not subscribing...

  • fuck off microsoft.

    You want to know how to cut a load of costs and improve customer satisfaction? Fire half your programmers and STOP CHANGING SHIT FOR NO REASON

  • It's awesome they're cramming in tons of integrations and AI for people that need/want that, but could they please just make a simple email/calendar client with almost no features?

  • We need a law protecting consumer data and privacy that allows users to turn off all AI features including buttons, scans, sharing, transmitting if you disable it at the OS level.

    • Well, after the government shutdown is over, go ahead, try getting your congressman's attention on this issue. Good luck.

  • But then again, it's Microsoft we're talking about here. They mess up everything they touch.

  • When it comes to IMAP - a well-documented and widely implemented e-mail protocol - Microsoft takes a "not invented here" attitude to it and has a disgracefully half-baked IMAP implementation of it in Outlook. Pretty well every popular non-Outlook mail client out there implements IMAP correctly, but a trillion dollar company called Microsoft apparently can't.

    My biggest grievances are that it often won't pick up changes to your IMAP inbox automatically and it doesn't implement the IMAP delete properly either

  • Are they updating the UI in Outlook, Outlook Classic, New Outlook, or Outlook (New)?

  • That's great. But how about an Outlook rewrite that actually works and doesn't crash five times each workday?

    I usually have Outlook permanently on my third screen at the office. My favourite one is when I'm doing absolutely nothing with it, working in another application on another screen, and I notice a flickering on the Outlook screen. I can see the UI gradually disintegrating, toolbars moving around, areas turning black and purple, elements disappearing, before the whole thing crashes and restarts. Happe

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