The search function is useless

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

The search function doesn't find anything.

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

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.

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.

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.

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.

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

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.

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

The minimize button closes the application.

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.

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

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

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

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

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

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.

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.

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.

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.

There's a keyboard shortcut to send an email.

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