With free support for Windows 10 expiring on October 14, enterprises risk both security vulnerabilities and operational disruption if millions of devices are left unpatched.
According to Nexthink, extended security updates (ESUs) could cost organizations $7.3 billion in the first year alone.
Yet the numbers tell only part of the story.
Beyond the ledger, IT leaders face a strategic challenge: how to migrate millions of devices without disrupting productivity, employee experience, or compliance obligations.
The decision to stay or move isn’t purely technical – it’s a boardroom-level question that touches risk, finance, digital transformation, and workplace collaboration.
The $7.3 Billion Risk
Of the 1.4 billion monthly active Windows devices, around 420 million are deployed in commercial or public sector environments. Nexthink estimates that 181 million still run Windows 10, and by the end-of-support date, roughly 121 million devices may require ESUs at $61 per device.
“Moving from one operating system to another shouldn’t feel like a disruption. It should be an opportunity to improve how employees work every day,” said Tim Flower, DEX Strategist at Nexthink.
“That means understanding how devices and applications perform before the migration, anticipating issues and problems, and taking steps to ensure migrations and upgrades run smoothly.”
For CIOs, CFOs, and IT directors, the question is not only the cost of ESUs. It is how to weigh immediate expenditure against the longer-term operational risks of staying on legacy software: rising maintenance costs, potential security vulnerabilities, compliance exposure, and slower response to changing business needs.
The decision also has financial implications beyond direct ESU costs. Extended use of Windows 10 can compound downtime costs, support calls, and lost productivity, particularly for organizations with large, distributed workforces relying on legacy systems for critical operations.
Migration Challenges: Stability and Operational Risk
Cost is just one side of the coin; migration itself carries operational risk. Nexthink’s analysis indicates that Windows 11 experiences more system crashes (1.2 percent vs 0.6 percent) and hard resets (9.9 percent vs 8.5 percent) compared with Windows 10.
These figures are not necessarily reflective of flaws in Windows 11. Instead, they often reflect hardware incompatibilities, driver issues, and deployment planning deficiencies.
“Every migration comes with teething problems, and what we’re seeing with Windows 11 is no different,” Flower added.
“These issues aren’t necessarily due to Windows itself, but are often linked to the underlying hardware, drivers, or the way systems are deployed. The lesson is that without visibility, IT teams are flying blind and deploying configurations that can be more prone to issues than necessary”
A poorly executed migration can result in lost hours, frustrated staff, and reputational damage, particularly in organizations where IT downtime directly affects revenue-generating operations. For IT operations teams, phased rollouts, testing on representative endpoints, and contingency planning are critical.
Enterprise teams also need to address application compatibility. Many line-of-business applications were built or optimized for Windows 10. Understanding which systems will transition seamlessly, which require updates, and which may need replacement is a complex but essential part of migration planning.
Turning Compliance into Strategic Opportunity
While migration carries challenges, it can also be a catalyst for digital transformation. Enterprises that approach the Windows 10 sunset strategically can achieve several benefits:
- Digital Transformation Enablement: Standardizing on a modern, secure OS lays the groundwork for cloud adoption, virtual desktop infrastructure, and more agile IT environments.
- Employee Experience Improvements: Windows 11 offers enhanced productivity features, integrated collaboration tools, and improved system reliability for modern hybrid workforces.
- Cost Management: While ESUs may seem a stopgap, strategic migration can reduce long-term IT support costs, minimize downtime, and optimize device lifecycle management.
Engaging the Full Tech Buying Committee
This issue touches multiple members of the enterprise tech buying committee:
- CIO / CTO: Strategic oversight of IT risk, compliance, and digital transformation initiatives.
- CISO / Security Officer: Exposure to vulnerabilities and regulatory compliance risks.
- IT Operations Managers: Device rollout, application compatibility, and support efficiency.
- CFO / Finance Directors: Cost-benefit analysis of ESUs versus migration investments.
- HR / Employee Experience Leads: Ensuring minimal disruption and enhanced productivity for staff.
- Procurement Teams: Vendor negotiations and licensing management for ESU or Windows 11 upgrades.
Ponder This…
Windows 10’s sunset is inevitable – but how enterprises respond is optional. Each device left on legacy software represents a potential security and productivity risk, yet each migration is also an opportunity to elevate workplace technology, accelerate digital transformation, and improve employee experience.
The question for boards and IT leaders alike is whether this will be just another compliance exercise – or a deliberate strategic move that repositions technology as an enabler of meaningful business outcomes.
