Microsoft officially sunset its support for the Windows 10 operating system.
As of October 14, 2025, security updates stopped, and customer service suspended technical support for this rather ubiquitous system.
With this change, it’s estimated that over 400 million devices are vulnerable to cyber threats without security updates. For CTOs and IT decision-makers, this represents the most significant technology transition challenge of the decade.
What can you do now that the deadline has passed?
A lot.
Just because Microsoft stopped supporting Windows 10 doesn’t mean people stopped using it.
A ControlUp study of more than one million enterprise endpoints in mid-2025 revealed that half of enterprise devices were still running Windows 10, despite the looming deadline.
This is a problem.
Think of it this way: You wouldn't leave your office doors unlocked at night, yet continuing to operate Windows 10 systems without security updates is exactly that—leaving digital doors open for cybercriminals who are already circling, waiting for businesses to make this mistake.
Organizations that assumed they could simply "wait and see" now face the reality of operating in an increasingly hostile digital environment without Microsoft's protective umbrella.
Successful CTOs understand that Windows 10 end of life support consequences extend far beyond individual workstations—they represent a shift in how businesses must approach cybersecurity and operational continuity.
The most dangerous assumption business leaders can make is that cybercriminals aren't paying attention to end-of-life transitions. They are—and they're preparing.
A good example is CVE-2025-29824, a zero-day vulnerability in the Common Log File System (CLFS) driver that Microsoft confirmed was actively exploited in the wild. Attackers used it to escalate privileges on compromised machines, deploy backdoors, and ultimately launch ransomware campaigns against companies in IT, real estate, finance, retail, and software development across several countries.
This isn't an isolated incident. Verizon's 2025 report reveals that 70% of breaches exploit known vulnerabilities—exactly the type of security gaps that accumulate when systems stop receiving patches.
Every Windows 10 system operating without security updates becomes what cybersecurity experts call a "permanent soft target." Unsupported devices will likely become these “permanent soft targets”, and attackers are likely to increase their focus on industries or geographies where migration lags.
The windows 10 end of support security risks compound daily. When vendors stop shipping fixes, known vulnerabilities become persistent attack surfaces, especially dangerous when large swaths of the installed base share the same unpatched code paths—attackers can scale exploits into widescale compromises rather than chasing small, isolated targets.
Compliance is an important operational and reputational component for companies. Many regulations, including HIPAA for healthcare, PCI DSS for finance, and GDPR for data privacy, require businesses to use supported, up-to-date software as part of their security controls.
Carrying that thought out, after Windows 10's end of life, any computers still on Windows 10 will fail to meet these standards since they won't receive security updates.
The consequences could be anything from fines and penalties to suspended operations.
Beyond regulatory penalties, there's the reputational cost. Non-compliance can hurt business opportunities—you may risk losing certifications or contracts if your IT environment isn't up to standards. Clients, partners, or vendors might require proof that you're using supported systems.
Every CTO faces the same fundamental question: What's more expensive—upgrading now or dealing with the consequences later?
Microsoft's Extended Security Updates pricing tells a story about urgency. Extended Security Updates for organizations and businesses on Windows 10 can be purchased through the Microsoft Volume Licensing Program at $61 USD per device for Year One, with the price doubling every consecutive year. This means Year Two costs $122 per device, and Year Three reaches $244 per device.
For an organization with 500 Windows 10 devices, the three-year ESU cost totals $213,500—money that provides no new capabilities, no performance improvements, and no strategic advantage. It's purely a penalty for delayed decision-making.
And you can’t buy partial periods—you must purchase by year (and if you join in Year Two, you must pay for Year One too, as ESUs are cumulative).
The hidden costs run deeper. Maintaining outdated systems typically increases overall IT costs through:
It’s also important to consider the opportunity cost. While your IT team manages the complexity of maintaining unsupported systems, your competitors are leveraging modern platforms to drive innovation and competitive advantage.
The math is clear: Proactive migration isn't just the secure choice—it's the economically rational one.
The most successful organizations approach major technology transitions with a structured methodology that minimizes risk while maximizing business continuity.
Here's your five-step action framework:
Document every Windows 10 device in your environment, including workstations, servers, and embedded systems. Start with business-critical systems that handle customer data or support revenue-generating operations.
Categorize each system by regulatory requirements and data sensitivity levels—this classification determines your migration priority sequence and helps justify budget allocation to stakeholders.
Lansweeper's inventory analyses found that roughly 42-43% of tested enterprise devices failed one or more Windows 11 minimum checks, including CPU, TPM, RAM, and UEFI/Secure Boot requirements. Understanding your hardware limitations shapes your migration strategy and budget requirements.
Calculate the total cost of ownership for three scenarios:
Factor in hardware refresh cycles, productivity impacts, and security investments.
Prioritize critical systems first, then roll out systematically across departments. For business-critical machines that cannot be upgraded, budget ESU enrollment or device replacement as part of the risk treatment plan.
For systems that must remain on Windows 10 temporarily, implement enhanced security measures: endpoint detection and response, network segmentation, stronger multi-factor authentication, and limited administrative privileges.
The key insight that separates successful transitions from chaotic scrambles is this: Start with strategy, not tactics. Organizations that begin with clear business objectives and work backward to technical requirements consistently achieve better outcomes with less disruption.
The October 14, 2025, deadline has passed, but your response window remains open. Every day you delay action, the Windows 10 end-of-support security risks multiply, compliance exposure grows, and costs compound.
The organizations that will thrive through this transition understand that technology decisions are business decisions. Windows 10 end-of-life support consequences aren't just IT challenges—they're strategic imperatives that require executive leadership and coordinated action.
Your next step is clear: Contact SymQuest's Windows migration specialists for a comprehensive assessment of your Windows 10 end-of-life support consequences and a customized upgrade strategy that protects your operations, ensures compliance, and positions your organization for sustained success.
Don't let outdated systems define your organization's future. The time to act is now.