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.

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

The minimize button closes the application.

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

Ctrl+f is not find

New Outlook pretends to support RSS, but there’s no way to trigger an update.

The search function is useless

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…

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.

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.

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

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

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.

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

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.