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.
this post was submitted on 06 Jun 2025
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My inbox view gets messed up every now and then and I have to keep resetting it.
An old bug that they're determined not to fix. It's been happening to me at 3 different jobs now
Outlook like many of Microsoft's products could really stand to be just eol'd and then replaced by a better product
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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.
I think the bad superscript is not a thing on the desktop app. I wonder if that's AI learning autocomplete
Trying to find the search button, depending on what you have open it is hidden completely.
Everything, fuck microsoft.
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.
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.
That I cannot export mailboxes to other clients. Screw .ost !
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
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.
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.
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?
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.
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.
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.
Having to use Outlook was a significant contributor to me leaving my last job.
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.