Goodbye Big FiveGoodbye Big FiveReporter Kashmir Hill spent six weeks blocking Amazon, Facebook, Google, Microsoft, and Apple from getting her money, data, and attention, using a custom-built VPN. Here’s what happened.

Week 4: Microsoft

When I initially planned to block all the tech giants from my life, I hadn’t thought to include Microsoft, mostly because Microsoft is—these days, at least—rarely on the receiving end of criticism for destroying civilization as we know it.

Microsoft’s days as a tech supervillain are a distant memory, dating back to the 1990s when 20 states, along with the U.S. Department of Justice, assembled like Voltron to take the tech company down for violating antitrust law.

But then I’m reminded that Microsoft is a web hosting giant when I see news in August that it threatened to pull its hosting services from Gab because of the social network’s anti-Semitic content. And since November, Microsoft has been competing with Amazon and Apple for the title of most-valuable public company in the world. This all forced me to admit that Microsoft is still fully deserving of its inclusion in the “Frightful Five” along with Amazon, Google, Facebook, and Apple. If nothing else, I think, it will be interesting to see the long-term effect of that decades-old antitrust crackdown: Will it be easier to block Microsoft because the government tried, at the turn of the 21st century, to prevent it from unfairly dominating the computing industry?

To prevent myself from using any of Microsoft’s services, I connect my phone, computer, and smart devices to a custom VPN designed for me by technologist Dhruv Mehrotra; it blocks the 21,573,632 IP addresses controlled by Microsoft. If you’re like me and exclusively use Macs, you might think you don’t use Microsoft very often. But it operates the workhorses of social media—LinkedIn, Skype, and Github—as well as a big distraction from work in the form of Xbox. During the block, I can’t use any of them, nor can I connect to websites and apps hosted by Microsoft Azure, its rapidly expanding cloud business.

Even though I don’t use any Windows machines, don’t own an Xbox, and don’t turn to Microsoft Office for document creation, the company still turns out to be tricky to block, not so much online, but in the real world, where Dhruv and his VPN can’t help me. In one surprise example, I run into the Redmond giant in my car—a 2015 Ford Fusion, which I have from a long-term rental service called Canvas. I’ve been driving it for weeks but only now notice a placard on the center console that reads, “SYNC, powered by Microsoft.” Turns out, Microsoft’s technology powers the car’s entertainment and navigation system, so I have to drive to work in silence.

(This is actually one of the last Ford models where that’s the case; Ford dumped Microsoft reportedly because its software was too buggy. Now Ford offers services from Google and Amazon. “Ford and Alexa, a match made in tech heaven,” claims Ford’s website, which sounds like anything but my idea of the divine.)

When I tell Dhruv about this, he points out that there are many more places I could potentially be using Microsoft services without realizing it, like when I buy coffee at a coffee shop that uses Windows as the operating system for its payment system or when I use public transportation that uses Microsoft to power its back-end services. As the New York Times points out, Microsoft is “mainly a supplier of technology to business customers.”

That means that Microsoft is virtually impossible to completely avoid without also retreating from society entirely, which, at least for me, isn’t an option. Just as Amazon was inescapable on the web, Microsoft is unavoidable IRL.


So Microsoft is in many ways a “B2B” company these days, and it’s undeniable that I rely on services at some point this week that use its services when I patronize restaurants, coffee shops, stores, or anywhere else where monetary transactions happen. But in terms of direct consumption of Microsoft products, this is the easiest week in my tech-giant-blocking experiment so far. Microsoft is still a behemoth but one whose impact is hard for me to measure in this experiment, because many of its billions of dollars come from products like Windows Servers that are used to power government and corporate infrastructure, rather than being used directly by consumers.

Not to say consumers aren’t using Microsoft products on a large scale: Windows still accounts for 40 percent of all operating systems accessing U.S. government websites, including iOS and Android, which is a pretty good indication of its general prevalence. It’s just not an issue for this consumer. As I admitted in the intro to this series, it reflects my own tech biases. Avoiding the company while functioning in society is probably impossible, but it is possible, I find, to avoid personally using Microsoft’s products.

Maybe this is the way things would have gone regardless of what happened in the 1990s. Maybe this was the kind of company Microsoft was fated to become. Or maybe, if the government hadn’t intervened decades ago to keep Microsoft from dominating the world of computers, we’d all still be using Microsoft-owned Hotmail and surfing friend feeds on Microbook and posting our photos to Microgram and Binging our latest health concern.

Number of times Kashmir’s devices attempted to connect to the companies she blocked.
Illustration: Jim Cooke (Gizmodo Media Group)

That decades-old Microsoft antitrust case was sprawling and complicated in the way that any legal matter is, but it boiled down to a rather simple catalyst. Windows was the dominant operating system 30 years ago, as it is on PCs still today, and the internet was only just starting to develop. In 1994, a company called Netscape released a popular internet browser called Navigator that it was selling for about $50, and Microsoft decided to undercut it.

To try to ensure its dominance in the growing business that was the internet, Microsoft developed its own internet browser called Internet Explorer, gave it away for free, and insisted that it be bundled with Windows. So when you bought a computer—which was probably operating Windows because most then computers did—you’d get Internet Explorer installed by default the same way you get Safari pre-installed on your iPhone or the Google Play Store pre-installed on your Android phone, which gave Internet Explorer a distinct advantage.

Microsoft was using its powerful control of the computer operating system supply line to muscle its way into controlling people’s internet experience (Netscape eventually made Navigator free as well, helping to lay the groundwork for an internet where almost everything is “free” but monetized instead via our attention and data.) Regulators worried that Microsoft was using its dominant position in the software industry to crush competitors and would-be competitors, and so they sued.

Giving Internet Explorer to people for free was seen as ultimately hurting consumers, which is a version of antitrust law that American regulators have since mostly abandoned, though activists like the Open Markets Institute are pushing for it to be re-embraced. It’s an approach that Europe recently adopted, as evidenced by its antitrust crackdown on Google last year; European regulators fined Google $5 billion for making its search engine the default and including the Google Play store and the Chrome browser for free in Android operating systems, which are used by 80 percent of smartphones.

The government originally hoped to break Microsoft up into two companies (one that made operating systems software and another that operated the rest of their products), which is similar to what tech company critics are calling for today for companies like Facebook and Google.

But the only concessions the government ultimately got from Microsoft after a years-long battle were a promise not to conspire to keep competitors from being excluded from new computers and a commitment to make Windows interoperable with non-Microsoft software. Still, that was significant, according to law professor Tim Wu and U.S. Senator Richard Blumenthal, who wrote in a New York Times op-ed that those concessions opened the door for the rise of new technology companies:

[W]hat we do know is that the remedy pushed Microsoft to act with more caution, creating an essential opening for a new generation of firms. It might seem like a cruel irony that the immediate beneficiaries of the Microsoft antitrust case—namely, Google, Facebook and Amazon—have now become behemoths themselves. But this is how the innovation cycle works: It creates room for saplings to grow into giants, but then prevents the new giants from squashing the next generation of saplings. (Microsoft was itself, in the early 1980s, the beneficiary of another antitrust case, against IBM, the computing colossus of its time.)

The then-new technology companies that thrived due to the government throttling Microsoft’s growth are now dangerously large and powerful, according to antitrust critics. But regulators, in the U.S. at least, have raised very few concerns about monopolies. Amazon, Facebook, Google, Microsoft, and Apple, combined, have bought over 400 companies and start-ups over the last decade, with none of the acquisitions facing pushback from regulators, as the Wall Street Journal points out.

“Today’s titans tower over their kingdoms, secure behind their walls of user data and benefiting from extreme network effects that make serious competition from startups nearly impossible,” wrote Antonio Garcia-Martinez in Wired recently about the lessons learned from the Microsoft legacy. “U.S. antitrust laws, written in the industrial age, don’t capture many of the new realities and potential dangers of these vast data empires. Maybe they should.”


Over the course of my week blocking Microsoft, my devices try to send over 15,000 data packets to the company’s servers, or just as much data as they tried to send to Facebook when I was blocking it—not much compared to Google (over 100,000) or Amazon (nearly 300,000). Most of the interaction with Microsoft is a steady stream of about 1,000 packets each night that mystifies me and Dhruv until we realize it’s when I open up my library book app to read before going to sleep, an app whose data must be hosted by Azure. I could read what I had already downloaded—the Wheel of Time books, because I’m a sucker for fantasy series destined for TV—but because of the attempted interaction with Microsoft in the background while I am doing so, I abandon the book for the week.

I’ll reiterate here that this low level of interaction with Microsoft might be unique to me, or at least unusual. Lots of readers probably have a Windows machine at work, or watch their favorite shows on a Surface tablet, or use Outlook for their corporate email, and wouldn’t find the Microsoft block as seemingly easy as I did. And even I, who thought I only relied on Microsoft for LinkedIn, Skype, and apparently, my car’s radio, realized through this exercise that I probably interacted with it in the real world, in coffee shops or paying my fare on the bus, in ways I couldn’t capture this week.

The big difference between Microsoft and the others in the Big Five is that it’s been forced into the shadows while the others are freely operating their respective empires right in our faces all the time.

So if the conclusion is that I can live (sort of) without Microsoft today because of the government’s antitrust crackdown in the 90s, the question is what the government should do now about the behemoths I am finding I can’t live without.

Next up: Apple

This series was supported by a grant to Dhruv Mehrotra from the Eyebeam Center for the Future of Journalism.

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About the author

Kashmir Hill

Kashmir Hill is the deputy editor for the Special Projects Desk, which produces investigative work across all of Gizmodo Media Group's web sites. She writes about privacy and technology.

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