this post was submitted on 06 Jun 2025
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Obligitory "I have to use it for my job," so let's commiserate.

It's the worst program in all of the Office Suite. MS wrote the goddamn OS and email client, but for some reason if I have two instances open for two different inboxes and try to pull one up on the taskbar, the wrong instance will pull up every single time without fail.

My runner-up complaint is how when I use the search bar, sometimes it'll forget what I'm doing and when I hit enter it'll open some email instead of executing the search.

Every update makes it worse, so what drives you crazy?

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[–] scytale@lemmy.zip 12 points 1 week ago

The calendar view can't be configured to fit a full 24 hour day and you have to scroll.

[–] teamevil@lemmy.world 11 points 1 week ago (1 children)

Bullshit left click for spell check now... constantly trying to think for me and distracting me with endless USELESS popups, no spell check in the subject like. It's awful

[–] LifeInMultipleChoice@lemmy.dbzer0.com 4 points 1 week ago (1 children)

You are getting pop-ups in Outlook? What version of Outlook are you using if you don't mind me asking.

[–] teamevil@lemmy.world 4 points 1 week ago

Not Pop up ads, constantly trying to suggest what I am about to type.

And we're using whatever version of part of Microsoft 365

[–] knightly@pawb.social 11 points 1 week ago* (last edited 1 week ago)

New Outlook pretends to support RSS, but there's no way to trigger an update. You read your feeds on Microsoft's schedule or not at all.

[–] kindenough@kbin.earth 11 points 1 week ago

Important emails from contacts I had for years flagged as spam.

[–] qevlarr@lemmy.world 10 points 1 week ago* (last edited 1 week ago) (3 children)

Meeting requests tracking, oh my god. It's a great feature but it's got so many quirks.

Once you decline a meeting, it's gone for good in your calendar. If you accidentally declined, you need to ask for another invite. More commonly, plans changed and now you can't attend when you could have because you forgot all about it.

You can't decline important meetings and still see them in your calendar, so people abuse 'tentative' as 'I want to know when this meeting takes place but I won't attend myself'

Can't organize a meeting and then don't attend yourself. Impossible. Neither can you transfer ownership when you're going on holiday for example, so people are stuck with meeting requests nobody can change

Good luck getting a long series of meetings accepted by a meeting room. Every single instance must be available, that's annoying but makes sense. You can cancel or move individual instances until the meeting room accepts it, but everyone gets spammed with invites.

After you made all manual changes and the meeting room finally accepted it, if you make any changes to the series, everything is reset and the manual adjustments starts all over

If you have to move one or two specific instances to a different room, you can't! You can move in time or cancel an instance, but using the next available room is not possible. Both rooms will decline

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[–] entwine413@lemm.ee 9 points 1 week ago (1 children)

Every once in a while it just decides it's going to completely change the layout, and there's no simple way to get it back to how it was.

[–] radix@lemmy.world 5 points 1 week ago

I've been using MS products for some 40 years, and I swear it's company policy to put every Chaotic Evil new employee immediately onto a UI/UX team. Absolutely zero consistency between products and versions.

[–] Saltarello@lemmy.world 9 points 1 week ago (1 children)
  • Randomly removes email addresses I use every day from the auto-complete forcing me to type them literally in full for weeks until it remembers them again.
  • A colleagues name starts "tom..." but it ALWAYS auto-completes with another colleague "tim...". Every single time.
  • Search sucks. Not sure if this particular complaint is just our company setup but for some reason it hides stuff older than a given date "on the server" which means you have to remember exactly where stuff is & open the folder before it displays the contents rendering search pointless. Absolutely hopeless
[–] psud@aussie.zone 3 points 1 week ago

search sucks

The workforce where I work is diverse, so often it's easier to find someone by their first name, but you're not doing that in outlook's address book when names are in "surname, given name" format

Likewise when the address list was changed to "first name surname" you could no longer find someone with just their surname

[–] DarkFuture@lemmy.world 9 points 1 week ago (1 children)

As a help desk tech, please don't get me started.

But in the spirit of contributing to this post...focused inbox. No Microsoft, I actually wouldn't like to see all my messages and would prefer if you could hide them from me so I miss important shit and get chewed out by my boss.

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[–] gedaliyah@lemmy.world 8 points 1 week ago

Like 2 years ago the search was really good. I'm always using referencing or updating all documents. So being able to find them quickly is a huge help in my day to day.

The search bar used to work almost instantly and find anything matching the title or even content in any document I wanted. Now even typing in the exact title doesn't pull up the document I'm looking for half the type.

[–] maxprime@lemmy.ml 7 points 1 week ago

Adding a group. You can now only add one email address at a time. Got a group of 100? Best clear your afternoon.

[–] Hegar@fedia.io 7 points 1 week ago (1 children)

Not being able to unpin email chains unless you change it to non-threaded replies, select all, unpin, then go back to threaded replies like a civilized lifeform. Otherwise it just repins the chain when it refreshes.

Our office also uses teams phones which still don't have a way to show missed calls. We literally cannot call people back if we don't get to the med room phone in time.

Oh wow, you may have just solved the issue I've been having with email chains I pin coming back! I'll have to give that unpin trick a try--thank you! That workaround shouldn't be necessary, of course, but I'm happy to have another option to try to unpin some of the long-past-relevant conversations that have been pinned in my inbox for over a year 😅

And thank you as well for the info about Teams phones. Some folks at work floated the idea of switching to Teams phones instead of our current VOIP setup, but if they don't show missed calls, I'm glad that idea never came to fruition!

[–] bizarroland@fedia.io 7 points 1 week ago (2 children)

One thing that I hate about it is, if a notification pops up and you are on a different screen or in a different app, when you mouse over the notification to click it to go away, rather than sending the notification away, it sends it to the background and brings outlook to the front.

So you then have to minimize outlook or move it out of the way to get to the notification screen to close the notification screen.

Also it continuously disables extensions because it's so fucking prioritized on minimizing boot-up time that it does not give a single fuck about how much extra time you have to waste re-enabling the goddamn extensions that you need in order to do your job.

We're paying good money for these extensions.

We want them.

We don't care about 1.3 fucking seconds of time it takes for Outlook to start up as long as we have the functionality, and Microsoft's Outlook keeps disabling them.

If this were a single computer, it would be a hassle. But this is company-wide, having to constantly train and go over how to re-enable the extensions that we need to keep enabled in order for our employees to do their fucking job that we're paying Microsoft $25 a month per person for.

or how about how Microsoft forces, Microsoft accounts to be created, but won't allow Microsoft accounts to be created using organization credentials.

But then it goes behind your back and creates a Microsoft account for every single organization credential.

And then it hides that from you inside of Edge so that you first have to remove the organization credential from Edge and then do a search and then remove the organization credential from being inside of Edge just to stop Edge from having an organization credential that it uses to track every single user in your organization and every single thing that they do.

So yeah, fuck Microsoft.

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[–] YoiksAndAway@lemmy.zip 7 points 1 week ago (2 children)

Setting up calendar events with reminders that never happen. At some point, they just stopped working for me.

[–] zout@fedia.io 8 points 1 week ago (1 children)

I tought that was me! This week I finally gave up on it, and started printing my calendar for the day. Welcome to 30 years ago I guess.

[–] YoiksAndAway@lemmy.zip 4 points 1 week ago (1 children)

I've been through pages of internet forums looking for a fix. The best advice I got was "set an alarm on your phone". I finally just gave up on outlook's calendar.

[–] zout@fedia.io 4 points 1 week ago

Yeah, for work I also have the outlook app on the phone, and that's even worse; some kind of overwatch policy prevents me from getting pop-ups reminding me which meeting I have, instead prompting me that I have a calendar event, and I should open outlook to see what it is. Then I have some additional hoops to jump through to actually view, so I gave up on that years ago. For now, a piece of paper it is.

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[–] CompactFlax@discuss.tchncs.de 6 points 1 week ago* (last edited 1 week ago)

The new version written in JavaScript and spite. Everything about that.

When you have the calendar open it refreshes and blinks while it does that, like every 15 minutes. This never happened with 2016

And people pay through the nose for that crap?

[–] Poem_for_your_sprog@lemmy.world 6 points 1 week ago* (last edited 1 week ago) (1 children)

There's a keyboard shortcut to send an email.

[–] psud@aussie.zone 4 points 1 week ago* (last edited 1 week ago)

And that keyboard shortcut is exactly the same as the keystroke to insert a line in other applications

I have a rule set up to delay outgoing email 2 minutes almost entirely because of how often I hit ctrl+enter

(Add format to a line, it formats that line and the paragraph above it; "no outlook, I want a paragraph break between those, not two linefeeds" <ctrl+enter>)

[–] Itsamelemmy@lemmy.zip 5 points 1 week ago

I resend a lot of email. Reply all, update subject, screenshots etc. A few seconds after you reply all, above the to field you start getting status updates. You're not replying to the latest email. This will be sent to xx people etc. It shifts all the fields down, so my click into the subject to remove the RE: is now editing the cc field instead.

[–] Rentlar@lemmy.ca 5 points 1 week ago

Are we talking about Outlook or "New Outlook"? Everyone that I've heard that switch to new Outlook has had nothing but pain that you can't "do the thing" you used to any more. Like "Meeting with All".

[–] Manifish_Destiny@lemmy.world 5 points 1 week ago

It's made by raccoons that live in a PCP factory dumpster. Also why the fuck do we need 4 different teams applications

Fuck Microsoft.

[–] fedev@lemmy.world 4 points 1 week ago (1 children)

My inbox view gets messed up every now and then and I have to keep resetting it.

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[–] Crozekiel@lemmy.zip 4 points 1 week ago (1 children)

Jesus. Basically everything about it. We use the web client at work, so might be a different set of annoyances.
deep breath I use slashes in 70% of the e-mails I write as the punctuation mark that they are - I have never and will never want it to start randomly guessing what files I want to attach to the e-mail when I type a slash.
I actually didn't hate that if you typed something like "23rd" it would make the rd super-script - until the day it started doing it so incredibly wrong that it would super-script the '3' and the 'r' and change the 'd' to a 'th' so it read "2^3r^th".
Several times per day it will show a folder name in bold with a number in parenthesis telling me I have new messages in that folder, but when I click on the folder it highlights nothing as new messages, so I have to just remember what the last message I actually read was. Search sucks. Rarely can I open attachments. I told a coworker just yesterday that if they want to keep something secret from me, their best bet is to put the secret in an e-mail attachment and e-mail it to me.

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[–] wingsfortheirsmiles@feddit.uk 4 points 1 week ago

On the new Outlook, clicking on emails that pop up opens them... in the background. Insane design choice

For some reason, opening attachments is a lot more painful that it needs to be in open emails.

Maybe there is an option to remove "open file in browser" but if there is I haven't found it. Awful, awful design

[–] Blue_Morpho@lemmy.world 4 points 1 week ago (1 children)

I have two instances open for two different inboxes and try to pull one up on the taskbar, the wrong instance will pull up every single time without fail.

That sounds like how everyone always guesses wrong which way to plug in USB, not a specific problem with outlook.

Labels should be the default but UI designers on all platforms only care about appearance. Googling says you can change the taskbar to not combine instances and show labels. That way you always know what you are clicking.

[–] Zombiepirate@lemmy.world 3 points 1 week ago

I can see the windows with the inbox labeled in the taskbar preview, it just consistently brings up the wrong one when I click it.

Believe me, I've tried for years to fix this.

[–] the_riviera_kid@lemmy.world 4 points 1 week ago

Everything, fuck microsoft.

[–] datavoid@lemmy.ml 4 points 1 week ago

When you try to change views in a shared calendar, and it automatically switches to your personal calendar in the other view, causing you to go back to the first view, change calendars, then do the exact same thing again.

Every. Damn. Time.

Also cached exchange mode is a disaster...

[–] HubertManne@piefed.social 3 points 1 week ago

honestly their office suite is something I feel they did overall pretty well with. Granted plenty of changes and little things that aggravate me but hard to say as Im not actively using it. Outlook and excel in particular are standouts.

[–] kyub@discuss.tchncs.de 3 points 1 week ago

Its popularity.

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