Microsoft’s Security Issues: Why the Company Is Failing

Microsoft has been rocked by one security breach after another, leading to major scrutiny and questions about why the company seems incapable of warding off bad actors....
Microsoft’s Security Issues: Why the Company Is Failing
Written by Matt Milano
  • Microsoft has been rocked by one security breach after another, leading to major scrutiny and questions about why the company seems incapable of warding off bad actors.

    Microsoft Security Issues

    Microsoft has had one major breach after another in the last few years, including the following:

    While data breaches and cybersecurity threats are becoming more common, it’s worth pointing out that Microsoft’s two biggest competitors—AWS and Google Cloud—have not experienced a single major breach of the magnitude of any one of Microsoft’s, let alone all of them.

    What Others Are Saying

    Needless to say, Microsoft has taken significant flak for its security issues.

    • Tenable CEO Amit Yoran said the company was “grossly irresponsible” and bordered on “blatantly negligent.”
    • Senator Ron Wyden has called out the company’s “negligent cybersecurity practices” and “shambolic cybersecurity practices.”
    • Homeland Security’s Cyber Safety Review Board found that Microsoft’s email breach “was preventable and should never have occurred. The Board also concludes that Microsoft’s security culture was inadequate and requires an overhaul.”

    Why Are Microsoft’s Security Efforts Failing?

    There are a number of significant factors that are contributing to Microsoft’s issues.

    Microsoft Software Is Ubiquitous

    One of the biggest factors in Microsoft’s security issues is that the company’s products are used everywhere. Windows is still the dominant operating system in the desktop space despite losing ground in recent years. Individuals, companies, organizations, governments, and government agencies use Windows.

    As a result, for decades, there has been no greater and more desirable target for bad actors than the Windows operating system. Compromising it opens a potential gold mine of opportunity, given the number and breadth of Windows users.

    The same is true of the company’s office and email products. In fact, they are so popular that they are used on competing platforms, such as macOS, iOS, and Android.

    Microsoft’s Services Are Tightly Integrated

    Microsoft leveraged its dominance on the desktop to expand into other markets, including the cloud and messaging. In fact, the company has integrated its services so much that it has run into regulatory trouble for unfairly leveraging its dominance on the desktop, leading the company to back off some of its bundling efforts.

    That integration, however, helps make the company a prime target, in many ways more than its competitors. For example, while AWS is the largest cloud provider, Amazon does not have a desktop operating system or office suite. In contrast, because Microsoft’s products share code, libraries, and more across desktop and server products, compromising one Microsoft product can open the door to possibly compromising many of them.

    Microsoft’s Insistence On Backwards Compatibility

    Microsoft is famed for providing backward compatibility, allowing users to run software that is years or even decades old.

    That backward compatibility comes with security risks. As the application and development landscape has changed, modern applications are built with security best practices that were not even thought of years ago. As a result, running those apps on a modern OS requires various measures to safeguard the system from an app that potentially represents a security risk.

    Unfortunately, none of these measures are fool-proof, and there is always the risk that a bad actor can exploit an issue, escalate privileges, or find another way to use an old app to compromise a modern system.

    Microsoft’s Transition From Desktop to Cloud

    Microsoft started as an office suite and desktop OS maker before branching into a plethora of other internet and cloud-based services. Unfortunately, this puts the company at a disadvantage compared to its younger competitors.

    Companies like Google and AWS benefit from their services being designed and built from the outset for the internet and the cloud, with the necessary security and safeguards built in from the ground up.

    In contrast, Microsoft had to adapt much of its code, products, and services from a single-user desktop environment to a multi-user internet/cloud environment, complete with the plethora of security differences that come with that.

    Microsoft Has “Missed-Out Syndrome”

    Microsoft has a long history of missing out on some of the tech industry’s most significant shifts. The company botched its attempts to capitalize on the MP3 player bandwagon, completely blew the smartphone revolution, fumbled the rise of usable tablets, missed the boat on search, and was late to transition to the cloud. Microsoft execs have publicly lamented the company’s failures in some areas.

    Unfortunately, whenever a company and its executives develop “missed-out syndrome,” it can set a company up for failure. When new opportunities arise, the fear of missing out once again can cause a company to move too quickly, make reckless choices, and not put the necessary safeguards in place.

    While no one outside of Microsoft can be 100% certain of the mindset within the company, some of its security issues have resulted from such amateurish mistakes that it’s hard to argue the company isn’t suffering from “missed-out syndrome,” rushing ahead without the proper safeguards.

    Microsoft’s Culture Is Currently Incompatible With Strong Security

    It’s hard to analyze Microsoft’s security issues without comparing it to its long-time rival, Apple. Despite starting as a personal computer company and having highly integrated services, Apple has not been plagued with security issues like Microsoft has. What accounts for the difference?

    In many ways, the difference comes down to culture. Since Apple began its turnaround under Steve Jobs, the company has firmly focused on protecting user privacy. To be clear, privacy and security are not the same thing. Nonetheless, many overlapping design principles and factors go into creating private and secure systems.

    As Apple expanded beyond its core hardware and desktop OS, it focused on creating private and secure products and services for its customers, sometimes to the company’s detriment in other areas. For example, focusing on on-device processing and consumer privacy has made it more difficult for Apple to compete in the AI market.

    In contrast, Microsoft’s culture has often revolved around partnerships, collaborations, and sharing data with other companies. As a recent example, the company’s Outlook email and PIM software now share data with 801 other companies. There’s an argument to be made that when a company is not focused on user privacy, it also impedes its ability to provide a truly secure experience for its customers.

    Unfortunately, this culture has permeated Microsoft from the top down. Founder and former CEO Bill Gates famously voiced his belief that Microsoft and other companies should cooperate with the NSA to provide back doors into products for the intelligence agency to exploit.

    Unfortunately, as security experts and mathematicians have explained ad nauseam, there is no way to create a back door for the “good guys” to use that won’t also be exploited by the “bad guys.” The fact that the founder of Microsoft doesn’t understand that speaks volumes about the security culture within a company whose software is used by the majority of organizations around the world. In contrast, Apple has always understood this principle and fought tooth-and-nail against the security back doors that Microsoft happily embraces.

    It’s no wonder that, as outlined above, the US government’s own review board found “that Microsoft’s security culture was inadequate and requires an overhaul.”

    What Happens Next

    Given the litany of issues Microsoft faces overhauling its security model, it’s unclear exactly what will happen next. One thing is clear, however: Lawmakers and regulators’ patience is growing thin.

    Senator Ron Wyden recently announced draft legislation to end the government’s “dependence on insecure, proprietary software,” largely in response to Microsoft’s repeated and devastating data breaches. Senator Wyden’s legislation would “set mandatory cybersecurity standards, save taxpayers money, and break the anti-competitive lock-in effect caused by proprietary, walled-garden software.”

    “My bill will secure the U.S. government’s communications from foreign hackers, while protecting taxpayer wallets. Vendor lock-in, bundling, and other anticompetitive practices result in the government spending vast sums of money on insecure software,” said Wyden. “It’s time to break the chokehold of big tech companies like Microsoft on government software, set high cybersecurity standards and reap the many benefits of a competitive market.”

    Others have come out in favor of Senator Wyden’s legislation, endorsing elements of the legislation that run contrary to Bill Gates’ views.

    “Through this legislation, the federal government has the opportunity to set an example for workplaces, organizations, and institutions across the country on how to fundamentally improve online safety. Protecting digital communication with end-to-end encryption is essential to data privacy and security, and should be the standard across the board. Without it, messages can be intercepted and abused by hackers, repressive law enforcement agencies, foreign governments, or the company that owns the platform itself. Everyone from the former director of the NSA, to Big Tech companies, to human rights defenders working under authoritarian regimes have highlighted the life-saving importance of end-to-end encryption. The issue of data privacy has never been more urgent, and decisive lawmaker action is needed in this moment to bring about tech platform policies that truly center our privacy and needs as users—not corporate profits,” said Leila Nashashibi, campaigner at Fight for the Future.

    If Senator Wyden’s legislation becomes law, Microsoft will stand to be the biggest loser and will only have itself to blame. The company has a small window of opportunity to completely overhaul its culture, making security and privacy core components moving forward.

    Whether the company’s leadership has what it takes to do so is another matter; only time will tell if they can overcome decades of heading in the wrong direction.

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