Sadly, Now We Need to Talk About OneDrive (Premium)

Enshittification is that sense of betrayal you get when a personal technology product or service you use and rely on turns on you, exposing the harsh reality that the needs of its maker are more important than your own. This doesn’t usually happen suddenly, though there are triggers that make it seem that way. Instead, it usually happens slowly, over time, as part of a creeping devolution during which the benefits you rely on are overwhelmed by bad behaviors that get in your way, annoy you, or actually prevent you from accomplishing the task for which the product or service was designed.

This isn’t how things should work. One’s relationship with these products and services, and their makers, should be consensual, a win-win. If you pay for something, for example, you should expect to get the expected service. If you don’t, you should understand what the trade-off is—ads, perhaps—so you can make an informed decision. Either way, you win because you want or need that thing, and its maker wins because you are paying them and will perhaps like the thing so much that you will adopt more of their offerings and then pay them even more. This is the very definition of a symbiotic, healthy relationship.

But enshittification turns this transaction on its head. It turns what was once healthy into something toxic. And as tech journalist Corey Doctorow, the inventor of the term, so ably explains, once you understand enshittification, you see it all around you. You see it in how the feeds on Facebook and Instagram have changed from a series of updates from friends and families into a never-ending cavalcade of sponsored posts and unwanted portrait-mode videos of idiots. You see it in search results everywhere, which favor paid placement over the organic answers you want.

And you see it in the Microsoft ecosystem. Everywhere.

Consider Windows 11, which begins selling you on additional Microsoft services during setup, and after forcing you to sign in with a Microsoft account. It puts sponsored app shortcuts in your Start menu. It pops up reminders to adopt more Microsoft services. It tracks your activities online without telling you and then doesn’t offer a way to turn that off. It forces you to use Microsoft Edge even when you, like over 95 percent of users, chose another browser, just so it can put your eyeballs in front of Microsoft services and ads. And so much more. On and on it goes.

But there is one growing form of enshittification in Windows 11 that is quickly rising to the top of the list. And that’s because it’s been getting steadily worse, like all enshittification, and is about to step over the line, jump the shark, and reset the value equation. And because there is nothing you can do to stop its horrible behaviors. Literally.

I am referring to OneDrive.

And that breaks my heart. I use OneDrive. Hell, I rely on OneDrive, as it’s the center of my daily workflow. Worse, I recommend OneDrive to anyone who will listen, and aggressively preach the gospel of storing your most important documents, photos, and other files in the cloud to ensure that they are always available, no matter which device you’re using or where you are in the world. I use it for its resiliency, its efficiency, its quality, and its value.

And now I sit here, betrayed.

Because OneDrive, for all its benefits—and there are many—is now succumbing to an enshittification process that started with the first version of Windows 11 and has gotten worse in each subsequent version. And as we as a user base lurch into the Windows 11 version 23H2 era, OneDrive’s creeping enshittification is finally reaching that trigger point where the sum of its problems is pushing me over the edge and forcing me to ask questions and consider alternatives. The cons are starting to outweigh the pros. And I could not be more unhappy about this.

To be clear, this is not something superficial. It’s not about surface-level user interfaces or little pop-ups I can easily disable using the Settings app. No, this is about deep-seated behaviors, a strategy whose aim is as unclear to me as are the problems it makes for me and other users. This is pernicious and malicious. And we need to rise as one, complain, and get this fixed. Microsoft, for all its faults, has proven quite receptive to this kind of feedback.

First, let me step through the enshittification we’ve already seen in OneDrive, and specifically in Windows 11 (and probably Windows 10, I just don’t use that anymore).

In the initial version of Windows 11, Microsoft instituted a policy that many saw as malicious: If you were setting up or clean installing Windows 11 Home, you had to use a Microsoft account (MSA), but if you were doing so with Windows 11 Pro, you could choose a local (“offline”) account. This changed with Windows 11 version 22H2, which requires an MSA for both product versions. (There are workarounds.) There are lots of reasons for this requirement, among them OneDrive: When you sign into Windows 11 with an MSA, OneDrive is automatically configured and available in the file system via File Explorer and other apps.

This is tied to OneDrive integration across the Microsoft ecosystem. For example, back in 2018, Microsoft introduced a feature called OneDrive Folder Protection to Windows 10 that let you sync your local Desktop, Documents, and/or Pictures folders with the corresponding top-level folders in your OneDrive cloud storage, a feature now called Folder Backup. (And in 2019, Microsoft made OneDrive the default Save location for Microsoft 365 apps like Word and Excel.)

In Windows 11, though, things got weird. When you installed Windows 11 Home and signed in with an MSA, which you were forced to do, Microsoft enabled folder sync on the Desktop, Documents, and Pictures folders during Setup whether you wanted it or not. But those who installed Windows 11 Pro were given a choice during Setup: They could opt out of this sync if wanted.

Well, that was the story. See, I’ve installed Windows 11 more than anyone you know, I bet, thanks to my endless reviewing of laptops and reinstallations of Windows 11 for my book and other testing purposes. And I’ve noticed something odd when setting up or installing Windows 11 Pro: Sometimes it works as advertised. But many times you’re not given a choice, just as with Windows 11 Home.

The solution to this problem, to date, has been to immediately open OneDrive settings when you get to the Desktop the first time and disable Folder Backup. I say “to date” because something just changed, but more on that in a moment. For now, consider the downsides to Folder Backup. Among them is that applications from Microsoft and many third parties, like Adobe, write data to your Documents folder, data that you may not want to be synced to the cloud, but especially not to other PCs. On the PC I’m writing this on, there is 2.5 GB of non-sensical data in there, taking up space and mucking up what should be a clean folder full of only my own documents. Ditto for Pictures, which has Camera Roll and Screenshots folders, the latter of which will sync through OneDrive even when you explicitly tell OneDrive that you do not want this crap synced: My Pictures folder should be a clean folder full of, wait for it, my own pictures.

But whatever. You may want this. You may not. At least you could disable it, ideally during Setup before it even happens.

This was always a problem, but in preparation for updating the Windows 11 Field Guide for Windows 11 version 23H2, I’ve prepped several PCs so that I am on this version as soon as possible. The issue there is that thanks to Microsoft’s Controlled Feature Release (CFR) functionality, which literally delivers individual new features randomly to customers, all of my PCs have had an inconsistent mix of the new features in 23H2. And so last night, I decided to Reset one of them to see if a clean install would perhaps deliver all of the features.

And … it did. That part of my experiment worked, so I now finally have a clean, full-featured install of Windows 11 version 23H2 on which to base my writing. Great. But this particular PC runs Windows 11 Pro, and during Setup last night, I explicitly disabled Folder Backup. I did a bit more work on it, went to bed, and then woke up this morning and started installing my apps (using the Winget-based bulk install method I describe in Roll Your Own Windows Time Machine (Premium). When that was done, I had several shortcuts on my Desktop. Which I deleted. And was confronted by a OneDrive dialog informing me that items I delete from OneDrive go to a Recycle Bin in the cloud.

A Recycle Bin in the cloud?

But I wasn’t using Folder Backup. And that means that the folder I had deleted those shortcuts from, Desktop, should not have triggered this warning. Huh.

And so I looked. And sure enough, in OneDrive settings, I could see that Folder Backup was configured. I turned it off, of course. And then had to manually delete all the detritus that had synced up to my previously clean OneDrive folders, and delete all the stupid “this is where your files are now” shortcuts that this configuration had left behind in my local folders. F@#$ing Microsoft.

This behavior is unacceptable. It’s bad enough that Windows Setup sometimes gives Windows 11 Pro users the chance to opt out of Folder Backup and sometimes does not. But now it ignored the choice I made and backed up those folders regardless.

And that is tied to another issue with Windows 11 and OneDrive that has been getting worse over the past two years, the constant harping to use Folder Backup. And that is about to get worse in 23H2 too.

For example, Microsoft updated the current version of Windows 11 (23H2) this past year to put a “reminder” in the User menu in Start to use Folder backup, and when you encounter this silly bit of nonsense, you’re given two choices, “Turn it on now” or “Remind me later,” and not “Stop asking.” You a probably disable this using one of the techniques I discuss in Windows 11 Personalization First Steps in the book. But there is some coming behavior that will be harder to disable, maybe impossible. (It’s early days.) In Windows 11 version 23H3, File Explorer now displays an annoying “Start backup” button to the left of its address bar whenever you browse into a local Desktop, Documents, or Pictures folder even when you’ve explicitly disabled Folder Backup. Microsoft really wants you to use Folder Backup.

The question is, of course, when will this become mandatory? After all, Microsoft made MSAs mandatory, first in Windows 11 Home and then in Pro. Microsoft then made folder backup mandatory (or at least automatic), first in Windows 11 Home and then sometimes in Pro. Will it take the next logical step and make Folder Backup mandatory/automatic? It’s a reasonable assumption.

As bad, there are still three versions of the OneDrive app in Windows 11 today, and which you get is semi-random. When you clean install Windows 11 (any version, including 23H2, oddly) you get the first version, which uses an old school Desktop interface without the Windows 11 look and feel. But over time, you will likely be upgraded to the new user interface that debuted with no announcement or explanation in December 2022. One version of this UI lets you back up two folders (Desktop, Documents, and Pictures), while the other lets you back up five (Desktop, Documents, Music, Pictures, and Videos). And right now, I have fully updated PCs with all three versions of OneDrive. Which is ridiculous.

(Tied to this, the new Windows Backup app only supports “backing up”—it’s really syncing—those first three folders. Even though the latest version of OneDrive supports five folders. Classic Microsoft.)

And then there are the sync issues.

The key to OneDrive, and I know this sounds obvious, is that it just works. And by “just works,” I mean that I can be sitting here writing this article in Word, save it to a folder anywhere in OneDrive via its Files on Demand file system integration, get up, walk into another room, open a laptop, browse to that file system location, and open this document and get right back to work. In the time it takes me to walk that far, this file should have synced.

And it does, usually. But one thing I’ve noticed in recent months, and especially during my digital decluttering work in August/September, was that this system doesn’t always work. And that to fix it, I had to force quit OneDrive and restart it to get it to sync each time. You see, there’s something missing from OneDrive that seems obvious to me. It doesn’t have a “Sync now” button you can use when it’s not working. And it needs one.

When you add up all these new behaviors, and perhaps some I’ve forgotten in my blind rage, you can see the scales tipping. That the benefits of OneDrive that once outweighed the cons are slowly being overcome by the latter. That me needing to constantly babysit whether this thing silently enabled a Folder Backup feature that I explicitly disabled is a step too far in this cycle of Microsoft disrespecting my preferences and choices. That OneDrive is working against me more than it is working for me.

And the problem with that, of course, is that the logical alternatives—Google Drive, which I do already pay for, or something like Dropbox, which I do not—will likely have their own issues. But I just want to get work done here, not respond to pop-ups, ads, and other annoyances while doing so. And maybe it’s time to experiment. Which I was sort of already planning to do, with Google Drive.

This is disheartening. Windows 11 should be better. OneDrive should be better. And the two of them? They should be better together.