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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[–] Crozekiel@lemmy.zip 4 points 6 days 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.

[–] psud@aussie.zone 2 points 6 days ago

I think the bad superscript is not a thing on the desktop app. I wonder if that's AI learning autocomplete

[–] lengau@midwest.social 2 points 6 days ago

Having to use Outlook was a significant contributor to me leaving my last job.

[–] prole@lemmy.blahaj.zone 2 points 6 days ago* (last edited 6 days ago)

I started using Outlook365 in browser during the pandemic, and never switched back. Not that much better, but I prefer the web app running in Firefox to the actual program.

Plus, at this point, if I even opened Outlook proper, Windows would probably freeze while trying to index all of the emails that have come and gone since the last time I opened it.

[–] thatradomguy@lemmy.world 2 points 6 days ago* (last edited 6 days ago)

Idk why MS lets you use add-ins but then they go and disable it if it starts misbehaving according to Microsoft's determination of it doing so and not the actual add-in causing problems. OH—and then guess what? You can't fucking enable every add-in. For some, you can only tell Outlook to not disable it for a month and then it's the same thing all over again. Fucking Microsoft!

EDIT:

Also, who is the bird brain that decided it was a good idea to force add-ins to be managed partially via the browser? Like if I click one of the manage Add-in buttons in the Outlook app, it works just in Outlook but the other one opens up browser.

Also also, why tf are there 2 different Outlook apps now? Why should an image have Outlook New and Outlook Classic? Why tf does the mail app even exist at this point?

[–] DemBoSain@midwest.social 2 points 6 days ago

When I click in the search-box in the titlebar, Outlook freezes for about 5 seconds.

You can't cut and paste an appointment.

I tried making a template the other day. I was successful, but it's multiple clicks whenever I want to use it. There's no way to customize the ribbon and add a button to use my new template.

[–] pineapplelover@lemm.ee 2 points 6 days ago

At work we constantly have issues requiring the need to recreate the Ms outlook profile. We made a script for deleting and adding back the ocp or whatever it's called

[–] SpicyAnt@mander.xyz 30 points 1 week ago (3 children)

We are asked to use Projects to manage our work, and we then mapped the project's structure into a folder structure using sharepoint. The thing is, this structure leads to very long file paths, and Windows won't let us open the files using the file explorer because the file path is too long, and so we need to search stuff through sharepoint, download as zip files, and end up breaking the intended organization. The projects page helps create the illusion of organization for the higher-ups but in reality it is a hindrance. We don't have admin access to the computer and so we can't change this file path limit setting. This is just the first that came to mind of an endless list of complaints I have.

[–] CTDummy@lemm.ee 12 points 1 week ago* (last edited 1 week ago)

Yeah SharePoint links are cooked. I copied a url from SharePoint and it crashed my remote session with someone and pretty sure its BSoD my device more than once. Upping the file path limit locally won’t help.

You can go to a SharePoint folder on the site and hit “sync” which will then add it to your file explorer if you have OneDrivs. Makes for easier navigation and collaboration. Fucked if I know how end users were meant to divine that.

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[–] stinerman@midwest.social 25 points 1 week ago (3 children)

It's another Electron app now. At least "New Outlook" is.

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[–] CodingCarpenter@lemm.ee 13 points 1 week ago (5 children)

I have to run it through a browser because I'm on Linux and it's constantly logging me out Even when I say don't do it don't ask again just keep me logged in. Nope fuck you log out, and sometimes it gets stuck in a loop where I log in and it logs me out immediately over and over until I clear my cache and reset my browser it's insane

[–] psud@aussie.zone 3 points 6 days ago (1 children)

I especially like this in MS Teams

It looks like it's working fine, then you try to join a meeting and randomly get one of:

  • It works
  • "We're setting things up for you" for up to 10 minutes
  • "Your organisation does not allow remote connections"
  • Automatically logs in like you authorised it last time

It always works fine if you close your browser and re-open it between uses of teams.microsoft.com

[–] CodingCarpenter@lemm.ee 2 points 6 days ago (2 children)

Have you seen the one where you're actually in a meeting and it warns that you've been logged out but still lets you continue your meeting?

[–] vrighter@discuss.tchncs.de 2 points 6 days ago

has been a long time since I used teams on my phone. It used to log me out constantly there too... but it kept sending notifications of all messages to the phone until I opened the actual app to be told I was logged out

[–] psud@aussie.zone 2 points 6 days ago

I haven't, but wow am I unsurprised

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[–] jeffw@lemmy.world 13 points 1 week ago (1 children)

I want to set an OOO. I don’t want the OOO to go to people who are emailing a group or list.

[–] OhNoMoreLemmy@lemmy.ml 5 points 1 week ago

Also, I want it to go to people outside my org that I email back, not random spammers and salespeople.

For some reason, the only option is to use people in my addressbook which doesn't auto populate and I never use.

[–] 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.

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

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

[–] teamevil@lemmy.world 11 points 1 week ago (2 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

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[–] knightly@pawb.social 11 points 1 week ago* (last edited 6 days 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.

[–] 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 6 days 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.

[–] 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.

[–] psud@aussie.zone 3 points 6 days ago

On the good side, when you miss a meeting because you're working from home and you were making coffee at just the wrong time, everyone believes you when you say you didn't get the notification

But legit, even when notifications are working properly they don't work well. They try to appear on top but will be behind anything that was opened as the notification triggered

[–] 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.

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[–] 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!

[–] 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.

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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?

[–] 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".

[–] 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

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