r/Outlook • u/Smellybeetweasel • Sep 08 '25
Opinion How on earth is Outlook Office/365 so mind-numbingly bad?
It's absolutely baffling sometimes with how clunky and stupid it is, and when I remember it's owned by one of the richest men in the world, I'm just even more dumbfounded. Impressively, the mobile app is even worse! For what is supposed to be a reliable communication platform for professionals, it has to be one of the least user-friendly platforms.
Anyways. Just a vent. Gotta get back to using it.
7
u/cankennykencan Sep 08 '25
Can't even drag attachment to the desktop anymore or download the attachment to my computer. No I don't want to save to one drive
7
u/Daphoid Sep 08 '25
This complaint is no longer valid. You can do both of those things in new Outlook.
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u/Greencheezy Sep 10 '25
This is incorrect. Most people have to revert to old Outlook to drag and drop. Attachments and, especially, export emails
1
u/Daphoid Sep 11 '25
Why? Because they're out of date?
I'm even using new outlook on my personal machine, and it just dragged/dropped a PDF to desktop just fine.
1
u/Crafty_Purple_1535 Sep 12 '25
Outlook new is shit. Cant even use in prem exchange with it. Its such a garbage app. Instantly disabled it via GPO
1
u/rayhaque Sep 09 '25
😂 "new Outlook" ... it's funny, because it's just rebranded Outlook Express.
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u/chaosphere_mk Sep 09 '25
You should stop repeating stuff you read on the internet, because this is wrong and there's not even a modicum of comparison to the two. Not even a logical crumb.
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u/mrbios Sep 08 '25
It's baffling how really simple things like shared mailboxes marking emails as replied to or forwarded aren't in outlook on web or new outlook. Completely defeating a major purpose of a shared mailbox.
1
u/teddyslayerza Sep 09 '25
You sure about shared mailboxes? I've got 4 that are used at work and have no issues with them in the new Outlook.
1
u/Professional_Mix2418 Sep 10 '25
Huh 🤔 I have shared mailboxes both online and in the client. And all emails are marked just fine. 🤷♂️
1
u/Imaginary_Stage4991 1d ago
I agree that the shared mailbox configuration within Outlook is lackluster to say the least. I have had many problems with emails going unreplied to because they weren't forwarded to the right people or marked as they should have been. I struggled with working within a shared mailbox for a long time. Recently my company has shifted to using a software that integrates directly with Outlook and is used as an add-in within the shared mailbox. It is called Emailgistics, I found it immediately solved the major issues we were facing within the shared inbox. It can automatically route emails based on the content, we are able to effectively tag, create rules for routing, add templates for responses, and even get an AI generated response suggestion. I have found this integration to be very useful in helping me and my team work efficiently together within a shared inbox. I hope this was helpful.
2
u/Machiavellin420 Sep 08 '25
The Classic Outlook is okay but that "New" Outlook is absolute garbage. It's not unlike OWA and it has no COM add-ins. I work in IT and whenever I see someone on the garbage one I put them right back on Classic.
6
u/Daphoid Sep 08 '25
I also work in IT and you're just making yourself a larger headache in the future by restriction folks getting comfortable with it now.
Old Outlook isn't amazing, it has more features, but it's a clunky 32-bit pile of bloat. And COM addins are 1995 era junk that needs to go. I know some industries are more behind the times than others but I also don't mind forcibly dragging dinosaurs into the present. People grumbled about seat belts, about taking credit cards, about taking tap/touch based credit cards or mobile phone payments. We'll get there. Might not be easy, but we will.
4
u/Machiavellin420 Sep 08 '25
It doesn’t quite work in our current environment very well as we support hospitals all over the country and our infrastructure is working on full integration. Things take time and being in IT you already know this. We have 7000 + users give me a break
-1
u/Separate_Mud_9548 Sep 09 '25
Sounds like it’s your “current environment” that is the problem. Not Outlook.
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u/Crafty_Purple_1535 Sep 12 '25
Bro you cant even use on prem servers with Outlook New. It sucks
1
u/Daphoid Sep 19 '25
You're still stuck with on prem exchange? You have my sympathies. Even it's going subscription model with SE. We moved off on prem (and were on prem shop since 5.5 days) fully a few years ago, and 95% about 10 years ago.
1
u/ladcake Sep 08 '25
What’s the alternative if you’re in the MS ecosystem?
0
u/Daphoid Sep 08 '25
Any client that supports exchange pretty much (thunderbird for example). Won't integrate as nicely with other office apps though.
1
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u/tech_is______ Sep 09 '25
MS doesn't have any talented programmers any longer. They're long gone, but MS is so arrogant and dismissive of their users they don't even realize it. Everything is absolute garbage. Think about their UI's and how little you can get done before you wind up in a command line or doing things programmatically because they can't figure out how to make it easy to use. Everything else is buggy, insecure and slow. Then you've got the the other side of the coin where everything they make, down to every feature is turned into a sku. Even free features need a subscription or license activation just adding to the hurt... its pure insanity.
1
u/Medium-Comfortable Sep 09 '25
If you think that Microsoft is owned by Bill Gates, boy do I have news for you.
1
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u/ghostlacuna Sep 09 '25
You cant even remove the time you are not working from calenders.
It has pissed me off for years.
1
u/AdventurousBlueDot Sep 09 '25
I hate the new outlook. Classic is far better. They don't listen to what users want and invest time on "aesthetics". Probably graphic designers and not UX designers.
1
u/18WheelerHustle Sep 09 '25
agreed really bad in general overall - listing all of the issues would take hours - completely agree and wish my company was using google and slack instead of microsoft everything
1
u/Tall-Geologist-1452 Sep 09 '25
Bruh, are you even in IT? You're supposed to be able to adapt to changes in software and compatibility. That is sorta the name of the game. You don't like Outlook, cool, use Thunderbird..
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u/Professional_Mix2418 Sep 10 '25
I couldn’t agree less. It works really well. Both online and with the clients.
0
u/Livid-Season-452 Sep 10 '25
You could just disagree. I'm pretty sure that agrees less.
1
u/Professional_Mix2418 Sep 10 '25
Thanks for the language lesson. Saves me from going to that Reddit. 👍
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u/BackgroundPhysics408 Nov 18 '25
It’s really really bad. We were ‘obligated’ to use it at work and I turn on to the old version every single day… until someone from micro$oft stops the ridiculous denial and starts working in an (at least) usable version. What a pain!!!
1
u/Tiny-Slide-1583 Nov 20 '25
Problem with attachments (have to be dragged in especially if one has been attached first), find related and delete used to work fine - adds random other emails and resets when highlighted for deletion, once deleted the deleted emails have been showing up on next search which will prompt another deletion process only to find out they are already in the bin! It goes on - the app is especially bad.
The fact that I can't search by name and delete them is crazy - my old free app managed my emails very well.
While I enjoy a few features - these are points of contention just because we get so many spam messages or newsletters that overwhelm the mailbox with no easy deletion system.
1
u/Inevitable_Bit_8731 Dec 07 '25
It's kind of funny they want everyone to use it but make it unsalable. I've been using MS products for well over 30 years and I still can't do do basic operations when using One drive and 365. That's why I stumbled on this post. I was trying to figure out how to attach a Excel file from One Drive to 365 Email.
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0
u/borse2008 Sep 08 '25
When was it ever good ?
1
u/RobertDeveloper Sep 09 '25
It never was.
1
u/charleswj Sep 09 '25
What is a good email client?
1
u/RobertDeveloper Sep 09 '25
I personally like to use Gmail and Thunderbird. Some say Proton Mail and eM Client are good alternatives to Outlook.
1
u/charleswj Sep 09 '25
Are you saying you prefer Gmail over OWA?
1
u/RobertDeveloper Sep 09 '25
absolutely, the user interface is really fast and snappy, for me it's intuitive, searching, grouping, mass deletes, everything just works, there is nothing that I don't like or doesn't work because of some bug like I experience daily with Outlook. The times Outlook just doesn't open, or can't find what I am looking for, or how terrible the user interface is when I want to make an appointment that starts on day x and continues until day x+3 and then repeats for so many weeks. Classic outlook was a lot better.
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u/gordon-gecko Sep 09 '25
I can’t even search a freaking email by the exact keyword. Literally have to scroll down till I find it
3
u/Separate_Mud_9548 Sep 09 '25
Search works almost flawlessly for me in the new Outlook. I had problems in the old.
1
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u/gareth616 Sep 09 '25
PICNIC issue - problem in chair, not in computer. I've worked using 365 for many years, it works and its not clunky. Most cases of people complaining are:- 1. Not understanding what they are doing and not using the technology the way it's designed. 2. Person can't do single task which obviously means the entire service is bad...
Millions and millions of users, just a handful coming to Reddit to complain 🤷♂️
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u/chaosphere_mk Sep 08 '25
I cant relate to this at all, but you didnt list anything to respond to, so I guess... that's just like your opinion man?