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Microsoft Accidentally Breaks Replying To an Email On Outlook (theregister.com) 70

Posted by BeauHD from the what-were-we-talking-about-again dept.
Microsoft has accidentally introduced a bug in Outlook for Mac that omits the original message from email replies, making it difficult for recipients to follow conversation history. Until Microsoft releases a fix, its suggested workaround is to roll back from version 16.110 and disable automatic updates, which is "great for users in full control of their devices -- not so good for anyone with a managed device," notes The Register. "Administrators with fleets of Macs running Outlook should brace for helpdesk tickets." From the report: In some instances, having a user copy and paste the salient bits of the email they are responding to might not be such a bad thing. We've all had emails that required epic amounts of scrolling to find what started the conversation, so forcing users to think about what they actually need to include is no bad thing. However, disrupting user workflows without warning -- well, that is undoubtedly a bad thing.

This is, after all, one of the most basic things an email client needs to do, so shipping a product with a bug that breaks this functionality says more about Microsoft's approach to quality than anything else.

Microsoft Accidentally Breaks Replying To an Email On Outlook More | Reply

Microsoft Accidentally Breaks Replying To an Email On Outlook

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    • Re: (Score:3, Funny)

      by Black Parrot ( 19622 )

      Nah, they're just jealous that other people's fuckups have been dominating the news, and they want some of that old-fashioned media love too.

    • That was almost exactly my reaction to the story, but I think you should have gone for funny with it. I'm also not sure you should have called it an "agent", however. So I have supporting anecdotes to share from my AI-supported "programming" experiences...

      My early experiments were mostly with ChatGPT and DeepSeek. My website was getting sick and the PERL/CGI was no longer allowed to run, so one of the many upgrade paths I explored involved moving functions, mostly statistical stuff, from PERL to JavaScript.

  • More importantly (Score:5, Insightful)

    by Valgrus Thunderaxe ( 8769977 ) on Monday June 22, 2026 @07:04PM (#66204942)
    That's going to break a PGP reply chain and the subsequent messages will be made unreadable.

  • Good that the headlines says accidentally (Score:4, Insightful)

    by rsilvergun ( 571051 ) on Monday June 22, 2026 @07:06PM (#66204946)
    It helps distinguish it from all the times Microsoft intentionally broke things in order to prevent interoperability with their rivals. I sure am glad that their illegal Monopoly was broken up back in 2000 and we didn't just elect a heavily pro corporate president whose doj dropped the lawsuit the first chance they got... That would have been terrible for computing.

  • omits the original message from email replies ... suggested workaround is to roll back ... [or] copy and paste the salient bits of the email they are responding to

    How about forwarding the message back to the sender(s), does the original still get included?

    • Re: (Score:2)

      by Malc ( 1751 )

      No, forwarding doesn't work either. For both reply and forward, all you get is the dividing line and the header info of the original message (sender, recipient, date, etc).

      Switching to new Outlook works, but then that comes with the bunch of other issues that makes me stick with legacy Outlook. That said, the previous update to this broken one also seems to have resulted in a bunch of missing emails, even after rebuilding my profile in a different folder and verifying that I can see them in new Outlook an

      • Re: (Score:3)

        by dfghjk ( 711126 )

        "I think Microsoft just aren't testing legacy Outlook properly anymore ..."

        CI/CD for the win.

      • If your version of outlook allows it, try pointing your server address to your OWA (outlook web access) URL instead of your actual exchange server. Not the prettiest work around but normally will at least pull everything you can see via OWA (when pulling from exchange leaves a bunch missing).

  • But I doubt it. (Score:5, Insightful)

    by msauve ( 701917 ) on Monday June 22, 2026 @07:18PM (#66204964)
    Perhaps they were trying to get rid of their god-damned forced top-posting.

    A: Because we read from top to bottom, left to right.
    Q: Why should I start my reply below the quoted text?

    A: Because it messes up the order in which people normally read text.
    Q: Why is top-posting such a bad thing?

    A: The lost context.
    Q: What makes top-posted replies harder to read than bottom-posted?

    A: Yes.
    Q: Should I trim down the quoted part of an email to which I'm replying?

    • Re:But I doubt it. (Score:5, Insightful)

      by Anonymous Coward on Monday June 22, 2026 @08:06PM (#66205010)

      Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.

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      But I must explain to you how all this mistaken idea of denouncing pleasure and praising pain was born and I will give you a complete account of the system, and expound the actual teachings of the great explorer of the truth, the master-builder of human happiness. No one rejects, dislikes, or avoids pleasure itself, because it is pleasure, but because those who do not know how to pursue pleasure rationally encounter consequences that are extremely painful. Nor again is there anyone who loves or pursues or desires to obtain pain of itself, because it is pain, but because occasionally circumstances occur in which toil and pain can procure him some great pleasure.

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      Why should I skip past boilerplate and old information to get to the important part?

    • Re:But I doubt it. (Score:5, Insightful)

      by rta ( 559125 ) on Monday June 22, 2026 @08:44PM (#66205036)

      Perhaps they were trying to get rid of their god-damned forced top-posting.

      Think of it as a reply with the previous conversation as an "FYI" attachment if you need to review context.

      In practice it works well, imo.
      In most simple cases you already know the context so don't need it. And if you do you can look down.

      And if you get forwarded an email or added to a convo mid thread, it's good to be able to first see the latest message to get some idea why you got the thing or what the request is, and then you can dive into the bg below. And yes in many of these cases i will scroll all the way down and read "up" which is not ideal but it's fine since it's relatively rare compared to the other usecase.

    • Re:But I doubt it. (Score:5, Funny)

      by JimWise ( 1804930 ) on Monday June 22, 2026 @09:36PM (#66205080)

      T > Perhaps they were trying to get rid of their god-damned forced top-posting.
      h >
      i > A: Because we read from top to bottom, left to right.
      s > Q: Why should I start my reply below the quoted text?
          >
      i > A: Because it messes up the order in which people normally read text.
      s > Q: Why is top-posting such a bad thing?
          >
      w > A: The lost context.
      h > Q: What makes top-posted replies harder to read than bottom-posted?
      y >
          > A: Yes.
      I > Q: Should I trim down the quoted part of an email to which I'm replying?
          > --
      s > "National Security is the chief cause of national insecurity." - Celine's First Law
      i
      d
      e
      -
      p
      o
      s
      t

    • A: Because we read from top to bottom, left to right.
      Q: Why should I start my reply below the quoted text?

      Because you've already read it. You might have even been the one to write it. New information goes at the very top. Reverse chronological makes perfect sense if you need to trace backward at a point of confusion because the most recent is the most relevant.

      • Re: (Score:2)

        by msauve ( 701917 )
        >New information goes at the very top.

        You must have a very interesting diary/journal. And it's really odd that syslog puts new stuff at the end - you should complain to the developers.

        • Those aren't communications. Communications protocols assume you have read up until the latest message.

        • Re: (Score:2)

          by BranMan ( 29917 )

          You could consider it a bug - when have you ever NOT auto-scrolled down to the end of syslog in order to figure out what just went wrong? If they wrote in reverse chrono order, you could just open the file and BAM! you'd see the relevant bits right in front of you.

    • Perhaps they could take a clue from software from 40+ years ago and make top-posting a configurable option.

      But Microsoft has pretty much completely given up on making their software configurable for user preferences.

  • Pretty weird use case! (Score:5, Funny)

    by BenBoy ( 615230 ) on Monday June 22, 2026 @08:55PM (#66205044)
    It's a pretty weird use case in an email client, replying to a message. Small wonder it was apparently left off of their automated regression suite, ja?

  • Or (Score:5, Informative)

    by hcs_$reboot ( 1536101 ) on Monday June 22, 2026 @08:59PM (#66205048)

    workaround is to roll back from version 16.110

    or just install Thunderbird.

    • On a Mac? Apple Mail works great even with 365 email. Thunderbird is not bad and definitely functional, but it is still not a polished UI after all this time.

  • and for those that can't, Microsoft will be glad to $ell it to you.

    For Mac users using Outlook to connect to non-Microsoft mail servers, Redmond ha$ a deal for you too.

    • Why, just why, would any mac users use Outlook? They could just configure their Outlook mail address to Apple's mail app, be it in macOS, iPadOS or iOS

      If they're that enamored w/ Outlook, why not just go all the way and get a Wintel laptop?

      • Fleet managed? Company has an old Exchange Server? They use windows at a different workplace?

        However, you are right. A sane person would use Apples Mail client.

        • Generally, if a company has decided to go w/ Exchange, then they would likely have gone for Wintel laptops in their fleet. Why go the Mac route, when those are more expensive?

          Macs make sense in a workplace where Apple had been the default platform. But if they went w/ that, they'd have picked a different email server platform than Exchange

          • Why go the Mac route, when those are more expensive?
            a) Because they are not more expensive.
            b) because they offer their high quality workers a choice: Windows, Linux, Mac
            c) because they run software, only available on Macs

            But if they went w/ that, they'd have picked a different email server platform than Exchange
            Because the previous moronic Sys Admin, picked exchange? He picked it because all in the office use Windows? Only the developers / artists use Macs?

            Now the new Sys Admin is shaking head every day, bu

  • New Outlook
    Classic/Legacy Outlook
    Web Outlook, but basically New Outlook

    • Outlook, along w/ Windows, is a poster child to demonstrate "Enshittification" of software. Classic/Legacy Outlook was fine, and so was Outlook Express back in the day. Microsoft obviously doesn't believe in "If it ain't broke, don't fix it", so like so much of other software of theirs, they kept updating it so that one has to re-familiarize oneself w/ the software, and keep disrupting their workflows

      This week, since my old Android tablet croaked, I migrated the accounts on it to a Chromebook of mine, a

      • "Enshittification" of software

        That implies that the software was actually good to begin with. Outlook never had that characteristic, unless your criteria for "good" includes good for passing viruses.

        • Re: (Score:2)

          by DarkOx ( 621550 )

          ok, full Office Outlook certainly had/has a ton warts but lets get real about it being 'good'.

          Rewind to 1997. There were some other really capable mail clients out there that really could manage very large 10k+ message mailboxes offline (key word for the time), the space got pretty rarefied as you started looking at elegant support for things like shared mailboxes or 'public folders' and of course mail integrated calendaring..

          Of the few options that remained suitable for large corporate mail deployments Ex

  • >"making it difficult for recipients to follow conversation history."
    >"so forcing users to think about what they actually need to include is no bad thing."

    Yeah, we kinda used to have such a thing. It was called "trim and inline reply" (bottom reply). Kinda like I JUST DID IN THIS POSTING. But, alas, that was not the Microsoft-way. So it turned into full bottom quotes just being added forever with top replies to 10 questions with no context.

  • Magic 8-ball says (Score:5, Funny)

    by Bu11etmagnet ( 1071376 ) on Tuesday June 23, 2026 @01:53AM (#66205204)

    Magic 8-ball says: Outlook not so good.

  • Microsoft's decline continues... (Score:3)

    by Smid ( 446509 ) on Tuesday June 23, 2026 @06:57AM (#66205342)

    A dumpster fire of an update, eh?

    Not the first in recent times. Last year my outlook client suddenly trashed all replies on the latest forced update in work. Went away three weeks later, quietly.

    My laptop still sits with a broken network on Windows 11, unfixable when I took the update three months later (don't use it much). No suggestions fixed it. It's to linux for me on that machine.

    I'd like to blame cost cutting or incompetence, but I'd say it's very likely Fake Intelligence evangelism on their part (others call it AI, that infers Intelligence, I don't).

  • Seems they've been breaking software (either by design, error, or accident) since I first encountered their applications in the late 1980s on a Mac. Ever since then, it just gets slower and slower as they forget to strip out the replaced code, and then 'forget' to keep the Mac version feature-equivalent to the PC version. It's fun when you're trying to explain to a novice MSOffice user that doing something specific that the MS website says is possible on the Windows version, just isn't possible on a Mac v
  • Apple already has a free mail program called.....Mail which can be configured to get your Outlook mail. But also means you PAID to have Outlook / Office on your Mac. Companies. ?? its suggested workaround is to roll back from version 16.110 and disable automatic updates, which is "great for users in full control of their devices -- not so good for anyone with a managed device,
  • My work phone is an iPhone, and we're required to use Outlook for work email. On average outlook gets patched twice a week for iPhone. The biggest flaw in it though has been there for years and clearly won't get patched.

    Namely, Outlook for iPhone always defaults to reply all for emails with multiple recipients. It doesn't matter how long the list is, it will reply all unless you go out of your way to reply only to the sender. This has catastrophic consequences at large companies.

    It is not uncommon

  • As long as I can get the vintage You've got mail! soundbite, I'll be fine.

  • "should brace for helpdesk tickets" ...except those will ALSO strip the thread from their replies.

    I'm constantly prefacing this boilerplate lately "It looks like your system lost the thread of the email that I sent, so I’m restoring that below for conversational continuity."

  • As useless as Teams (Score:3)

    by HnT ( 306652 ) on Tuesday June 23, 2026 @10:21AM (#66205668)

    M$ office as a whole struggles with the most basic functionality. Now they broke replying to an Email, for months the camera in teams only works occasionally⦠seriously, who is giving M$ all that money? This is way worse than nobody-got-fired-for-buying-IBM.

  • Why use Outlook on a Mac?
  • It's not a bug, it's a "feature"! In all seriousness though, why can't Microsoft go a single day without breaking something?
  • I'm not saying it is true, but I can imagine being assigned to Office Products for MAC is the Microsoft equivalent of Siberian Exile. In Soviet Russia, Macs program you.

  • ...that this was done by devops without saying it.

    NO regression tests were run on this update.

  • Every morning I log on to my work computer and get reminded that I have a choice between 2 versions of Outlook: The outlook I have have used for years or a new version with a less flexible UI and less features. They removed things I have used as a part of my workflow for years. Eat a dick, Microsoft.

  • Windows updates cause almost as many issues as the problems they're trying to fix in the first place.

    Linux / MacOs / SteamOS don't really have to try all that hard to increase their userbase.

    They only need to suck a bit less than what Microsoft is peddling as an OS these days.
    The users will migrate to the other systems on their own.

  • "...shipping a product with a bug that breaks this functionality says more about Microsoft's approach to quality than anything else"

    been like this for more than 40 years

  • Who needs the nonsense junk of the thread? You already have it, you replied to it, so what does sending it back to you again, and again, actually accomplish? If your email client can't follow the thread, and stack it for you, that's a fault of the email client. I don't remember when I started deleting the thread, but it's been years, and I wouldn't be surprised if I've been doing it for over 20-years.
  • Microsoft did something very similar a little over 5 years ago. May 11, 2021, early afternoon, a forceed update updated my Outlook aaaaand replies just open up as blank email. Had to use work arounds to frantically notify all my clients (who are also heavy Outlook users). Not a fun day! Why don't you check these things before pushing updates? Are your users just a joke to you??

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