Unsung Problems with Microsoft Accounts

Although I was initially skeptical about the direction where Windows 8 was headed, I’ve now become a full-fledged fan of Windows 8.1 Update. Yes, there are still some warts with Windows 8 UI and the app store is still mostly a joke.

Related: Revisiting the Windows 8 Tablet

However, Windows 8.1 Update is a great desktop operating system, and it’s also a great tablet operating system as well. What I think I enjoy most about Windows 8.1 Update is that it gives me a sense that Microsoft is still in the game and has tons of potential in their bid to unify computing experiences across several different form factors and devices. There's one aspect of going all in with Windows 8 that’s been driving me nuts—consistent problems and headaches with my Microsoft account.

The Microsoft Account Authorization Scheme

There are two major problems that I have with my Microsoft account. First, it’s entirely too easy for me to get locked out of my account. Second, there’s no simple way to unlock my account, as I’m forced to reset my password as part of the unlocking process.

Related: Microsoft Windows 8 Isn't as Bad as the Fear Surrounding It

In terms of how my account gets locked out, I believe it stems from me using my Microsoft account across so many devices, applications, and services. I see some irony here because that's how I believe Microsoft envisioned me using this account. Still, here’s a quick and informal list of just some of the software that I’m authenticating through my Microsoft account:

Windows Sign-In. Although I haven’t yet enabled this on my desktop, I do use my Microsoft account for sign-in on two of my tablets and on my wife’s laptop. All in all, this is pretty spiffy and helps keep settings and other details synchronized.

Visual Studio 2013. Every time I launch Visual Studio 2013, I assume that my Microsoft account is being used, because I opted to enable this functionality the first time I installed and ran Visual Studio 2013.

The stupid Mail application in Windows 8.1 on my primary tablet. The requirement to have to use a Microsoft account to even set up initial access or functionality of the Mail application on Windows 8 tablets is one of the things that makes the app a joke.

Microsoft Office. An Office subscription was a no-brainer for me. For less than $10 a month on the annual plan, I can license a family plan where I can install Office on up to five PCs or Macs, where Office is deployed on four PCs.

Other stuff. I’m sure I’m missing other applications and services that are mostly built into Windows that are occasionally trying to use my stored username and password to do… whatever it is that they do. And I’m not including things such as access to Connect or Azure here because although I do use my Microsoft account for those things, I assume they’re not routinely trying to phone home with old, cached credentials and locking me out. On the other hand, who knows? Maybe visiting MSDN documentation online is the culprit, as I still can’t understand why Microsoft does an almost transparent login and redirect half the time I’m viewing documentation (and, in case it’s not clear, yes: I’m being facetious).

My hunch is that somewhere among the bevy of devices, services, and applications that I have running with my single Microsoft account is that somewhere, some service or application is occasionally trying to log in with my credentials using an old or expired password. In turn, this means that all too frequently when I go to log in onto my Microsoft account, I’m greeted with a screenshot similar to the following:

Additionally, this means that I then need to go and jump through several different hoops to unlock my account.

The problem, however, is that I can’t simply unlock my account. Instead, I have to go in and change my password. To be frank, the process is a bit of a pain in the butt. Granted, part of the reason it’s such a pain is my fault, as I’ve enabled two-factor authentication as a protection for my account.

The biggest issue that I have is once I’ve defined a new password and recovered my account, I then have to stroll through the house, find all of my devices and go back in and try to change my Microsoft account password across any and all devices and services that I can think of – all hopefully before one of them phones home a few times on the old password to lock my account again.

To further complicate matters, not all of these applications seem to work the same way. Office, for example, gets very cranky when trying to synchronize OneNote notebooks after a password change, while Visual Studio 2013 still manages to keep me signed in without ever caring that I’ve changed my password.

Yes, I know I’m being a bit of a baby and that this really is a first-world problem. I also get that things are more complex than I’m perceiving them to be. My problem though is that I’m sure this isn’t just a case of me fat fingering or forgetting my password, simply because when this problem happens I only get one chance to log in and I’m quite confident I’m entering my password correctly. If the problem was me I’d expect at least two or three failed attempts. Instead, I routinely get one chance and then get locked out of my account at least monthly.

Most of the time I just ignore being locked out and stop trying to do what I was doing. As a result, I didn’t finish trying to buy the application that's shown above. And that, frankly, is not just a blow to the Microsoft applications store, but is also a blow to the developers that created the app.