I don't remember the last time I had a workday that didn't involve logging into something that I definitely logged into not very long ago, that I use every single day, and it's so, so, so fucking tedious.

And it doesn't escape my notice that all the fucking things I have to log into over and over and over are using Microsoft auth. Which granted, I think every office worker would notice that just from the ubiquity of their software, but still. And, on top of it, Microsoft's login flows are remarkably, consistently clunky. The forms jump all over the place and it has to refresh the page like 5 times as it's processing your credentials, and lord help you if Outlook needed you to sign in and silently opened that stupid auth window, because if you go through the entire thing, odds are great that you'll get a "security token expired, please do it again" message at the end. Like I dunno personally I wouldn't get a security token until the user has actually interacted in some way with the stupid form but what do I know I've only been making software for like 13 fucking years.

Oh yeah, bonus points: I use the passkey thing for my MS Auth app on my phone, and every single goddamned time I sign in, it asks me if I want to.... wait for it... create a passkey.

Edit: Oh oh and, for the above? If you're working through your morning coffee and accidentally click OK instead of cancel, it'll sit there spinning forever, not sign in correctly, and then you get to do ALL THIS BULLSHIT AGAIN.

Just, truly the biggest circus with the most clowns over there.

Microsoft's auto-logout appears to be implemented in the frontend. If I leave the Outlook or Teams tabs opened but idle for a few hours I get kicked and have to log in again, but I have an addon that will unload tabs I haven't interacted with for an hour, and one day I noticed that if I click away and intentionally let those tabs unload when I'm not using them, I can stay logged in for weeks or months.

Fortunately I don't have to deal with Microsoft professionally, but anything Xbox related is also such a massive pain. More than 3 times now I've tried to login and got into an endless login loop.

If you look that up you'll see that people have been encountering that for over a decade.

I simply and truly don't get it.

Microsoft must have at least 80.000 devs. No one there ever wanted to fix this?

I genuinely could not care less about it. Most of it is trivial click-through session validation (Github -> Microsoft auth -> Github) where most of the pain is solved by auto-redirect, the rest is auto-filled by my password manager - including 2FA, although that part is technically probably not the best idea.

If I ever have to manually fill anything in, it is almost certainly going to be a phishing attempt. It immediately jumps out as "this is unusual, something is wrong here".

The only thing which bothers me is email login links, but luckily I don't daily any apps which use them.

> lord help you if Outlook needed you to sign in and silently opened that stupid auth window, because if you go through the entire thing, odds are great that you'll get a "security token expired, please do it again" message at the end.

Whenever I see the Outlook auth box I mash in some gibberish for my password to immediately get the "expired" notice so that I can enter my real auth info.

So if any admin happens to look, my baseline for incorrect passwords entered is 50%.