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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[–] altphoto@lemmy.today 6 points 6 hours ago (1 children)

The fucking thing cannot search. I like to keep my email as conversation mode, but regardless if I get an attachment or I can remember some of the words in the email I would search for it and maybe 10% of the time I would find it.

It's incredibly frustrating how useless the search function is.

[–] Zombiepirate@lemmy.world 2 points 4 hours ago* (last edited 4 hours ago)

My favorite is when I search for something and nothing comes up, but I search again and it brings up a hundred results. So I have to search everything twice if there are no results just to make sure.

[–] helpImTrappedOnline@lemmy.world 2 points 6 hours ago

The minimize button closes the application.

[–] Aufgehtsabgehts@feddit.org 5 points 11 hours ago

Unreliable search, can't handle one online and one local postbox side by side (both have to be turned to online postbox), it messes up my contacts every chance it gets, rules don't work on the online postboxes,... And everything is so slow!

I am so happy with my Linux setup, but for this one costumer I have to use this shitty piece of software.

[–] Outwit1294@lemmy.today 2 points 11 hours ago

Sometimes tasks go to the trash randomly. It doesn’t happen consistently enough to see what causes it.

[–] JTskulk@lemmy.world 8 points 15 hours ago (1 children)

I use the web version and sometimes I'll be typing into the body of an email and it'll interpret my keystrokes as shortcuts outside of that email and start deleting random messages and closing the email I was writing.

[–] flubba86@lemmy.world 2 points 5 hours ago

I've seen this bug in the outlook web app too. Like it suddenly thinks I'm holding ctrl or something, then every keystroke in middle of typing an email become commands to mess up my inbox and delete my drafts.

[–] ximtor@lemm.ee 2 points 11 hours ago

You can't AND/OR combine filters. If i want to move stuff into "Gitlab trash" automatically, I need to use different rules instead of one with multiple applying conditions

[–] Timecircleline@sh.itjust.works 6 points 16 hours ago

I learned the hard way that "Delay Send" only sends when you launch the desktop client after the chosen time, instead of just sending at the chosen time like you'd expect.

[–] fushuan@lemm.ee 5 points 17 hours ago (1 children)

It's the worst program in all of the Office Suite.

I digress. The worst office suite program is Publisher.

I have never ever user it for anything, but for some fucking reason any company PC has it as a default program for .pub files, and that means that everyone that creates a new key pair and opens the pub file to copy it the gets lost and need special instructions to close that fucking thing and to open the file with notepad or something.

Fuck that program for choosing pub as their extension.

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

Nope, it's their CRM. I have actually written a chrome extension to deshitify their web app and have passed it around for my company to use. It hides clutter, the stupid copilot, those triple navigation bars that take up half the screen real estate, opens all notes, color codes some things.

[–] gerryflap@feddit.nl 3 points 20 hours ago (1 children)

Honestly what doesn't annoy me? The list is pretty short. I've never used Outlook before my work, I'm used to Gmail. Outlook feels remarkably shit for something so commonly used. Microsoft ia horrible at UI design imo. I can never find what I need and things that are supposed to be simple are somehow very convoluted.

[–] LifeOfChance@lemmy.world 2 points 17 hours ago

Exactly all this! Man, its like sitting on an uncomfortable chair but with my hands. I spend more time googling where something is or how to turn a setting off. It's awful.

[–] last_philosopher@lemmy.world 7 points 1 day ago* (last edited 1 day ago)

Being secretly not updating because it thinks it's disconnected, so I have to notice that little icon by the inbox to know it's just not telling me about meetings being scheduled and such

[–] rammer@sopuli.xyz 6 points 1 day ago

Outlook doesn't use email addresses to route e-mail with Exchange servers. Instead it uses some internal "address" that is longer than the actual e-mail address. This becomes a problem when an e-mail account is deleted and then recreated later. And the old internal address is still in some users Outlook addressbook. Because the internal address changes when the account is recreated.

[–] Macaroni_ninja@lemmy.world 7 points 1 day ago (2 children)

The search function is useless

[–] Tar_alcaran@sh.itjust.works 2 points 22 hours ago (1 children)

Outlook always forces me to categorize like it's 2005. I've got two dozens folders because shit is unfindable.

[–] Macaroni_ninja@lemmy.world 3 points 12 hours ago

Same. Also when I set rules to send stuff to specific folders sometimes I cant see them there, but if I search for the email specifically it finds it. WTF?

I found out by accident, when I was checking a new daily report and some dates were not visible in the folder, but I could find them via search.

[–] thatradomguy@lemmy.world 2 points 1 day ago

Doesn't help that when it does work, I can't delete everything it finds at one time. I have to repeat the search multiple times. Crazy

[–] WeAreAllOne@lemmy.dbzer0.com 2 points 1 day ago

That I cannot export mailboxes to other clients. Screw .ost !

[–] stiephelando@discuss.tchncs.de 11 points 1 day ago (1 children)

The search function doesn't find anything.

[–] Tar_alcaran@sh.itjust.works 4 points 21 hours ago

It actually finds LOTS of things, except what you're actually want

[–] lengau@midwest.social 2 points 1 day ago

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

[–] qevlarr@lemmy.world 8 points 1 day ago* (last edited 1 day 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

[–] gabelstapler@feddit.org 4 points 1 day ago

Once you decline a meeting, it's gone for good in your calendar. If you accidentally declined, you need to ask for another invite.

If you decline a meeting the original meeting will be moved to the trash. So go to trash and you can accept it again.

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[–] Bebopalouie@lemmy.ca 15 points 1 day ago (1 children)
[–] WhatAmLemmy@lemmy.world 3 points 10 hours ago

"What drives you crazy about MS Outlook?"

"YES"

[–] TheDoozer@lemmy.world 4 points 1 day ago

OneDrive crashes not only the original computer I had the problem on, but the replacement computer that I got (upgrade) as well. Then when I moved to a different office, it crashed another computer and then created the same problem for the one other person using the computer.

And by crashing, I mean the second it tries to do anything everything freezes, and the only way to get out of it is a hard reset.

So OneDrive.

[–] esc27@lemmy.world 22 points 2 days ago (5 children)
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[–] SpicyAnt@mander.xyz 30 points 2 days ago (2 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.

[–] laurathepluralized@lemmy.world 10 points 1 day ago (1 children)

Oh goodness, the Windows filepath limit has caused so many headaches at work. Even if you enable longer filepaths, not all applications pay attention to that, since at some point, Microsoft promised a specific filepath length and some applications hard-coded it in, so Microsoft is kind of locked in to supporting that being the default max filepath length. Not sure if any Office applications fall into that camp, but given that most filepath length errors I see are from Windows itself silently failing to finish extracting a zip archive, it wouldn't surprise me!

[–] 843563115848z@lemm.ee 4 points 1 day ago

This really sucks when part of the mandatory cloud file path name is "defense information systems agency". That eats up a lot of the available space.

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[–] prole@lemmy.blahaj.zone 2 points 1 day ago* (last edited 1 day 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.

[–] stinerman@midwest.social 24 points 2 days ago (1 children)

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

[–] Quazatron@lemmy.world 12 points 2 days ago (1 children)

This. You have to load a whole ******* web renderer context so that developers can more easily add "features" like emojis and animated gifs to a ******* mail client. Same thing with Teams.

It's all so woefully wasteful, slow, painful. But it's OK, we now have loads of RAM, fast SSDs, multi-core multi-thread ultra-fast CPUs anyway, and gifs really are a must-have in modern corporate communication.

Just get out of my lawn.

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[–] thatradomguy@lemmy.world 2 points 1 day ago* (last edited 1 day 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?

[–] Lemming421@lemmy.world 18 points 2 days ago (4 children)

I am willing to forget pretty much any fault on Outlook when I compare it with the absolute dogshit product that is New Outlook.

Click on a Toast and it opens the email… in the background, never in the foreground.

Have anything other than Email selected (calendar, for example) and it doesn’t display the New Email notification on the tile, so if you didn’t see the toast and have anything other then Outlook open in the foreground, you don’t know you’ve got new email until you physically go back to Outlook and click on the Email button.

Want to send a spreadsheet as an email attachment from within Excel? The option is there, but it doesn’t work any more (and the same for any other native “send via email” option in your OS out applications).

Want to send a document as an attachment? You have to open a new email, then drag the document into the correct half of the email, because if you have it too far to the left, Outlook will upload it into OneDrive and put a link to it in the email.

I could go on, but fuck me, it’s absolutely disgusting how much this breaks any previous workflow you may have had for doing email quickly and efficiently…

[–] Broken@lemmy.ml 4 points 15 hours ago

They keep pushing new outlook so hard, but it is still lacking basic features. Want to add a contact with a vcf file? Nope, can't do that. Want to have access to other email boxes? Nope, can't do that. Want to send an email without being prompted that you may have forgotten an attachment? Nope. OK OK, but they say its better and we should all use it. Fine, I'll bite. OK so can I get my mobile app to function the same way? Nope. No "new" app for mobile.

[–] PolarKraken@sh.itjust.works 3 points 1 day ago

Yeesh. I've been (blessedly) away from MS for a bit now so I'm kind of catching up / watching the carnage from afar.

When you jack up veteran user workflows so much that it makes the OS feel alien...you're really just daring people to jump OS. I know it's not that simple for work environments, but I can't imagine administering this sloppy mess has gotten any easier, so...gonna be fun waiting for the suits to eventually catch up I guess.

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[–] jordanlund@lemmy.world 13 points 1 day ago* (last edited 1 day ago)

+ That time they randomly slapped up this tool bar on the left hand side I neither requested nor needed.

[–] Saltarello@lemmy.world 9 points 1 day 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
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[–] DarkFuture@lemmy.world 9 points 1 day 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.

[–] gabelstapler@feddit.org 2 points 1 day ago

From my experience outlook flags emails as unimportant, that are quickly deleted, or deleted while being unread. So for me it's not too far off.

[–] jeffw@lemmy.world 13 points 2 days 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.

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