Complexity, Thy Name is PC (Premium)

The post-PC era spawned by the iPhone in 2007 impacted Windows in ways both obvious and subtle, and in ways both good and bad. Many of these changes can be seen as a virtuous cycle of sorts, where innovations that started in mobile are brought to Windows PCs, making them simpler or more efficient. But some of the changes are disruptive, leading to unintended consequences.

File sharing is a key example. In the pre-mobile world, Windows users would create shares so they could transfer files between PCs on a network. This process was technical and difficult, and with the rise of home networks, Windows XP introduced a simple sharing method while keeping the legacy system and renaming it to advanced sharing. But simple sharing was also too difficult for most users, so Microsoft created a different system called HomeGroup in Windows 7 to further simplify the process.

By the time Windows 7 arrived in 2009, the shift to mobile was already underway, of course. Web-based email was common, and for basic sharing needs, most people simply emailed files to themselves. And with USB storage getting faster and cheaper, we used the time-worn sneakernet method for sharing bigger or more files, with a flash drive or external hard drive replacing the floppies of the past. Most simply ignored the network-based sharing features in Windows.

To address this changing world, Microsoft then introduced the Windows Runtime (WinRT) mobile environment in Windows 8. Among WinRT’s many advances was a new Share contract system that allowed the operating system and its modern apps to support the sharing of files and other content. This was exposed as a Share charm and Share pane in Windows 8/RT.

And now everything is different, again. Well, almost everything.

If you’re familiar with all or some of these features, you may know the charms disappeared in Windows 10 and that the Share system feature continued forward, though few apps support this functionality today. And that HomeGroup soldiered forward until 2018, when it was removed in Windows 10 version 1803. And that system Share has since expanded with new functionality (that few use), especially in Windows 11.

Tied to all this, Microsoft in Windows 7 introduced the ability to link what was then called your PassPort online account to your local account sign-in, a system that Apple still uses today in macOS, albeit with its own Apple online account. Then in Windows 8, Microsoft introduced the ability to sign in to Windows using this online account, since renamed to Microsoft account (MSA), instead of a local (or domain) account. There are real security and usability advantages to using an MSA sign-in, but Microsoft began cracking down on local account sign-ins starting in the first release of Windows 11 to force the issue. You can still use a local account, but Microsoft makes it difficult.

So here we are in 2024. Most of us sign in to Windows 10 or 11 using an MSA. There are new methods for PC-to-PC file sharing that few know about, like Nearby Sharing. And there are methods for phone-to-PC sharing that don’t require a USB cable connection, like those built into the Phone Link app and third-party solutions like Google’s Quick Share (previously called Nearby Share).

But where the MSA giveth, the MSA also taketh away. The legacy simple sharing and advanced sharing features are still available today in Windows 11, like vestigial strata from the past. And if you’re a power user who still sees the value of this functionality, and you need to push lots of files across your home network, you may have discovered an unfortunate side effect of using an MSA sign-in: Those features don’t work anymore. They’re sitting there in Windows, mocking you. But they don’t work.

In writing the Windows 11 Field Guide, I wanted to document all the ways you can share files (and other things). And looking at this today, you can see that it’s incomplete. The book covers Nearby Sharing, but not the legacy file share functionality. And there’s no explicit Share coverage, though it’s mentioned throughout the book. So I’ve wanted to update that and offer a more complete view of file sharing in Windows 11. And that means I need to figure out how legacy file sharing—simple sharing and advanced sharing, technologies that date back to the 1990s—can work for the majority of us who sign in to Windows 11 (or 10) using an MSA.

To date, what I’ve found is a workaround that I wrote up as a tip back in January. Long story short, the simple and advanced sharing methods that still exist in Windows today were created at a time when local accounts were the only way for individuals to sign in to Windows. And they’ve never been updated to accommodate MSAs. And most likely never will be, since this functionality isn’t necessary for most people.

I recently came across a second example of this strata-based complexity, as I think of it. A few weeks back, I wanted to record an episode of Hands-On Windows about Windows 10, inspired by my reinstalling the system on a Surface Book 2 back in March. I love doing Hands-on Windows, but the show requires me to record the screen while I demo things, and it’s notable how many problems this has caused. Long story short, I didn’t feel that installing OBS Studio, the screen recording software I use, on the Surface Book 2 was a good idea. What I wanted to do, instead, was to use Remote Desktop.

For those unaware, Remote Desktop allows you to remotely access a PC, over the network, viewing and interacting with its desktop in a window that can be expanded to full-screen. Leaving aside potential latency and graphical issues, the effect is ideally similar to that when you’re using that PC directly. You can run apps, and do whatever it is you typically do with that PC.

(There are all kinds of limitations to Remote Desktop, of course. You can’t remote into a Windows Home-based PC using the tools built into Windows, though there are third-party solutions for that. You can’t play games successfully. Getting this to work over the Internet is another can of worms. Etc.)

Like network-based file sharing, Windows has offered Remote Desktop functionality for over two decades. And while this feature has its own sordid history, I’ll spare you that and just point out that it, too, predates the MSA as a sign-in, hasn’t really been updated in any meaningful way in quite a while, and it sits there in Windows, unused by most, like another vestigial reminder of the past.

More to the point, Remote Desktop, like the legacy file sharing features in Windows, requires a workaround for those of us—most people–who sign in with an MSA. Interestingly, there’s another caveat here, because Remote Desktop does work with an MSA. It just doesn’t work if your PC is using a particular default configuration that I suspect most of you have never once looked at or thought about, let alone changed. (I certainly hadn’t, and I write books about Windows.)

Put another way, to get Remote Desktop working today in Windows 11 or 10, you need to use a workaround. And I have now documented that workaround, a bit belatedly, in Tip: The Remote Desktop Workaround. I would have gotten around to this regardless—as noted, I want to add this type of content to the Windows 11 Field Guide too—but I was reminded to do so by a recent forum post. So thanks for that.

This workaround is tied to the way MSA sign-ins work in Windows 11 (and, I assume, Windows 10): When you first sign in, you must configure a PIN, which is the most basic form of Windows Hello. (If you have compatible hardware, you’re also encouraged to enable fingerprint or facial recognition as well, but you can skip this during Setup.) It is this requirement that breaks Remote Desktop, and there is an option in the Settings app, enabled by default, that prevents this from working.

You can check out the tip for more detailed instructions, but it’s interesting to me that, once you successfully connect to the PC remotely, you can go back and re-enable that option in Settings, and Remote Desktop will still work. Windows is not usually that accommodating.

But the point here—yes, there is a point—is that this legacy strata in Windows is paradoxically both key to the success of the platform and what’s holding it back in this modern age of simpler mobile platforms. And when I discuss the simplicity of ChromeOS or iPadOS, as I did recently in What If Snapdragon X Marks the Spot … for Chromebook? (Premium) and Thinking About iPad (Premium), respectively, this is what I’m talking about.

There are pros and cons all over the place here, and there’s no easy answer, no one thing that will work for everyone. And that’s why this is such a big discussion. Where one person sees power and functionality, another sees complexity and waste. I do feel that simplicity wins out in the end. But getting there is another story. Like many of you, I rely on, in some cases even prefer, some of the complexity inherent to the PC. And bridging the past with the future is a process, not a hard stop. We’ll get there. Or we won’t.