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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[–] [email protected] 12 points 1 day ago

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

[–] [email protected] 2 points 1 day 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.

[–] [email protected] 5 points 1 day 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.

[–] [email protected] 11 points 1 day 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

[–] [email protected] 4 points 1 day ago (1 children)

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

[–] [email protected] 4 points 1 day 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

[–] [email protected] 8 points 1 day 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.

[–] [email protected] 7 points 1 day 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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[–] [email protected] 9 points 1 day 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.

[–] [email protected] 5 points 1 day 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.

[–] [email protected] 7 points 1 day ago

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

[–] [email protected] 2 points 1 day 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

[–] [email protected] 7 points 1 day 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.

[–] [email protected] 3 points 1 day ago

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!

[–] [email protected] 6 points 1 day ago* (last edited 1 day ago)

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

[–] [email protected] 3 points 1 day 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.

[–] [email protected] 2 points 1 day ago

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

[–] [email protected] 5 points 1 day 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.

[–] [email protected] 6 points 1 day ago

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?

[–] [email protected] 6 points 1 day ago (2 children)

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

[–] [email protected] 3 points 1 day 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

[–] [email protected] 7 points 1 day 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.

[–] [email protected] 4 points 1 day 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.

[–] [email protected] 4 points 1 day 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.

[–] [email protected] 6 points 1 day ago* (last edited 1 day ago) (1 children)

There's a keyboard shortcut to send an email.

[–] [email protected] 3 points 1 day ago* (last edited 1 day 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>)

[–] [email protected] 5 points 1 day 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".

[–] [email protected] 4 points 1 day 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.

[–] [email protected] 3 points 1 day 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.

[–] [email protected] 4 points 1 day 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

[–] [email protected] 3 points 1 day ago

Everything, fuck microsoft.

[–] [email protected] 3 points 1 day ago

Trying to find the search button, depending on what you have open it is hidden completely.

[–] [email protected] 3 points 1 day ago

That it will automatically try to disable com add-ons even if you tell it not to or create a group policy that tells it not to disable certain add-ons. Still on some machines they will disable. Disabling and re-enabling them from the list often won't fix the issue as you have to first re-enable them in another menu. If neither work then you have to completely re-install the add-on.

[–] [email protected] 3 points 1 day ago

Its popularity.

[–] [email protected] 3 points 1 day ago (1 children)

Outlook like many of Microsoft's products could really stand to be just eol'd and then replaced by a better product

[–] [email protected] 5 points 1 day ago (1 children)

They did that. New Outlook.

[–] [email protected] 7 points 1 day ago

better product

No, they don’t do that part.

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