If you follow my blog for a while, you know I hate Microsoft. That’s a fact. But in this post, I will do a different take – a look at their products instead of the practices.

So, recently I had the experience of having to use Microsoft for business. This means… well, honestly, I don’t know what that means – and that is part of the problem. Am I using Office 365? No, it doesn’t seem so. So is it a Microsoft account? Again, no – logging in to it says that my account doesn’t exist. Is it Hotmail? No. Is it Outlook? Well, kinda – I do use outlook on this account, but if I go to outlook.com and try to login, it redirects me to login.live.com. So, my business account is a Microsoft Live account, right?

Well, no. Of course, not.

See, if I try to access Outlook, it does redirect to Live, but it adds some parameters to show that I am not logging into Live, and instead, to Outlook.

Am I nitpicking? No. The issue was – I wanted to add my USB Token as a MFA instead of using their Authenticator app. And how do you search for this? “I want to add a token into my outlook account” returns, as usual on Microsoft sites, something that is quite what you want but not really – so I need to be more specific, because if I search for “USB Token on Microsoft Account” it shows me how to add the token to “my profile” and I don’t have this tab because – guess what – Outlook is not “Microsoft Account” for some reason.

Then, you search things, and you find “AD”, “Azure”, “Entra”, “Hello” and other service names without actually explaining what they are. What I did was to search for “Microsoft my account add USB Key to login” and that got me the result. That’s right: Microsoft Account and My Account resolve to different instructions, and they are both different services and incompatible with each other.

So, I registered my device, added a PIN (because it’s required – why? Who knows) and now I have to type my e-mail password AND my key password to use my key…. which is annoying, so I decided to check how to change the PIN of the device. At first, I deleted and re-added it, just to find that, well, this didn’t work – it didn’t allow me to type a different PIN on the registration process.

So I found in the same link how to change the PIN: You can manage your security key settings from the Windows Settings app, including resetting your security key and creating a new security key PIN.. Great, another new service name – “Windows Settings app”. Googling this returns that it’s something that’s bundled with Windows.

So, let’s recap: I had to login into Outlook, that redirected me to Live, that I had to press My Account (that is different than a Microsoft Account) to register an USB device that now, to change the PIN, I have to use Windows – the operating system – that was never involved in the process, and that I actually don’t have. Did I get this right? Great…

… what they don’t mention is that you can do the same thing by visiting chrome://settings/securityKeys in a Chromium-based browser…

Now, to Azure. If you go to Azure, it’ll automatically log you into Azure using one of your accounts. Which one? Who knows, right? And it gets worse, because you can’t have both logged in at the same time, with the inconvenience that links to one service might send you cross-account to other service like Google did.

Yes, that’s right: Google, a company that’s famous for his horrible, disastrous implementation of multi-accounts, is better than Microsoft.

But again – since before the year 2000, they though that a single user account was sufficient to run their operating systems, right? And in a way, they still think that’s the case, so it’s not surprising that all this “I have a personal and professional account in Microsoft” is so weird and bizarre and uses different services that sometimes, but not always, integrate between each other. But honestly, in my opinion, this is less from a difficult from them to believe that multi-users is a thing, and more like the jankiness of every Microsoft system; we have to face it, like it or not, few Microsoft products actually have a good, clean, beautiful and straightforward interface.

Still, would it hurt too much to even… you know… try?