No, that's been the Outlook experience since probably forever.
this post was submitted on 04 Nov 2025
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I've been doing this for 15 years daily now and it was never this bad. Not even when everyone ran Exchange on-prem with al the bullshit involved with that.
I'm sure it's gotten worse since Microsoft fired QA and devs and replaced them with AI, but Outlook and Exchange have always been weird and buggy.
I personally haven't been a mail admin for a few years so nothing comes to mind, but similarly, the recent update to the Outlook mobile app, at least on iOS, moved the reply button from its prominent location to the message three-doy menu. Like the #1 thing people do with a message, that I'm sure their analytics show, was hidden in a menu.
Ill agree. But just FYI Azure AND aws have recently had downtime which funny enough can effect a lot of things with email. Since email in itself is more html nowadays than anything else. And ive had the same issue with 2FA and timeouts from Azure/cloud exchange. Fun times.
When I retire, im going to look forward to never touching MS product slop again. Should be fun!
Flick the switch to new outlook. It’s way less shit.
Apparently Microsoft is already planning to kill the "new" Outlook with some AI native "new new" Outlook. So don't get used to it too much I guess. Source: https://www.theverge.com/tech/806162/microsoft-outlook-ai-overhaul-notepad
Unless you want to send a hyperlink to a intranet address, then you're SOL.
Outlook classic is on life support. Next October Exchange Online drops support for it.
It’s built on decades of code. It allows plugins to directly affect the UX. It still uses I explore at times.
I switched to new outlook and while it has its own significant issues, at least it’s not spaghetti code. It also runs on top of Edge, which allows Outlook devs to ignore a lot of backend code, and makes the UX pretty consistent across platforms.
Sadly I'm still bound to classic Outlooks because of a lot of clients dependent on COM add-ins.
Yeah those com addins are usually the problem with outlook stability. Simply moving to modern addins improves Outlook classic significantly.
There is no simply moving here sadly, the plugins simply aren't available. Hooray for vendor lock-ins.
Have a similar issue in my industry. Microsoft went to a conference in my industry and straight up asked everyone there which vendor plugins are slowing down the transition and said they will be contacting those vendors directly.
Try dragging a folder inside another folder in your inbox and watch it disappear.
Remember when lotus notes was good?
The more shit you tack onto something the worse it gets.
Just remember, the only way to get a consistent experience across all users is to design to the least common denominator. In this case that means designing for a program that runs in an Internet browser.
That's why the more advanced features have been disappearing over time. That's why the older versions start having weird problems. That's why they are dumbing everything down and making it less powerful.. so it can run in edge.
Yeah, I use outlook in a browser and it's been doing weird shit I hate.i presume this to be by design.
If I try to add a hyperlink to an email it will insert the image I line, which isn't what I want. They added big obnoxious banners, and there's a placeholder advertising a premium version of outlook under it if you block it
I am just a user and not administering anything here, but holy fuck my mailbox is almost full, and yet I can't delete more than a couple of emails at once without crashing Outlook.
I can't believe how many wacky UI glitches this app has, and how many ways I can crash it from normal use. It's not my PC either - coworkers have similar problems.
Do it from the web man. Doing it from the app means it needs to sync twice. Do it in the web browser, right off the server, and you can mass delete shit all day long and just minimize the browser and keep working.
It is going EOL