Windows 11 Migration Deadline 2025: How Enterprises Can Prepare and Accelerate Transition

As enterprises worldwide approach the looming October 2025 deadline for Windows 10 end of support, a fresh landscape of both progress and peril has emerged, according to newly released data from ControlUp’s Windows 11 Readiness report. The study, which analyzed over one million enterprise Windows endpoints, reveals that half of managed devices have yet to complete the migration to Windows 11—an improvement over previous years, but still a cause for concern as organizations race against the clock.

A Snapshot of Enterprise Migration Progress​

In its announcement, ControlUp, a leader in digital employee experience (DEX) management tools, emphasizes a key milestone: only 50% of corporate Windows machines are now left to upgrade, a significant shift from the 82% lagging just a year prior. This rapid acceleration points to swelling momentum, driven by the impending end-of-life for Windows 10 scheduled for October 14, 2025. Despite this progress, the scale of the challenge is underscored by the fact that millions of endpoints remain vulnerable and at risk of running unsupported, unpatched operating systems if organizations fail to act swiftly.
“While the 50% completion mark is a major milestone, it's not time to relax,” warned Marcel Calef, Americas Field CTO at ControlUp. “With Windows 10 end of support just months away, organizations need to act now to avoid being caught off guard.”

Sector-by-Sector: Winners and Laggards​

ControlUp’s granular analysis exposes stark disparities across industry verticals. Education and technology are powering ahead, with 77% and 73% of endpoints running Windows 11, respectively. This early adoption is attributed to both sectors’ relatively newer hardware portfolios and policies prioritizing up-to-date digital tools—an investment that is now paying dividends in terms of streamlined transition.
Conversely, the healthcare sector continues to lag, with only 41% of devices migrated—closely followed by finance at 45%. Of particular note is the hardware hurdle in healthcare: 19% of healthcare endpoints are deemed incompatible, requiring outright replacement to support Windows 11. Finance, although behind in software rollout, faces far less hardware churn, with only 3% requiring replacement before migration can proceed.
This difference signals divergent budgets, procurement cycles, and risk tolerances. For healthcare, the high cost and operational disruption of hardware upgrades is a persistent barrier. In highly regulated fields like banking, protracted change management cycles and critical application dependencies slow the path to modernization despite technical eligibility.

Regional Readiness: The Americas Versus Europe​

Geographic differences further complicate the global migration picture. Enterprises in the Americas are furthest behind, with only 43% of endpoints running Windows 11. This is particularly striking because, according to ControlUp, 87% of American devices are technically “Windows 11 ready.” The lag stems not from hardware constraints but from logistical and organizational inertia.
In contrast, Europe emerges as the migration frontrunner, achieving 70% migration, followed by other global regions at 66%. The reasons for Europe’s lead are multifaceted: robust regulatory climates, tighter governmental guidelines on software currency, and centralized procurement practices enable faster, more consistent upgrades. For multinational corporations, however, the regional divide introduces risks of fragmented compliance standards and operational inconsistencies.

Scaling Up: Large Enterprises Face Steepest Climb​

Migration becomes more daunting at scale. Enterprises managing over 10,000 Windows endpoints report only 42% completion rates, the lowest across all organization sizes. These figures underscore the complexity of large-scale IT environments, where:

• Legacy hardware and applications proliferate, sometimes essential to business operations yet incompatible with new OS requirements.
• User groups are diverse and globally dispersed, requiring tailored rollout strategies and staged implementations.
• IT teams, despite access to advanced assessment tools, grapple with multifactor planning: inventorying, remediation, user training, and phased deployment—each step subject to delays and escalation.

For CIOs managing sprawling global fleets, the challenge is less about intent and more about orchestration: identifying upgrade-eligible devices, planning replacements, and ensuring that mission-critical functions are not disrupted during the switchover.

Tools and Tactics: The Role of Windows 11 Readiness Assessment​

The deployment of assessment tools—including ControlUp’s own Windows 11 Readiness Assessment, integrated into its broader ControlUp for Desktops platform—has proven vital for organizations aiming to cut through complexity. Such solutions enable IT leaders to:

• Instantly evaluate hardware and software compatibility across the diversity of their endpoint estate.
• Prioritize devices for upgrade, isolate those needing immediate replacement, and automate reporting for executive visibility.
• Identify pockets of risk—such as legacy applications or unsupported chipsets—that require special handling or phased retirement.

Marcel Calef highlights the platform’s ability to consolidate these insights: “Our data shows that the rate of migration is uneven and many enterprises still face significant hardware and planning challenges. ControlUp’s Windows 11 readiness assessment tool helps IT teams instantly evaluate endpoint compatibility, identify upgrade opportunities and flag devices needing replacement, all from a single dashboard.”

Driving Factors Behind Migration Gaps​

While the looming Windows 10 end-of-support date is a compelling motivator, ControlUp’s research surfaces several persistent obstacles:

Hardware Obsolescence​

The single greatest challenge across lagging sectors is legacy hardware. Microsoft’s Windows 11 hardware requirements have been more stringent than prior versions, notably requiring TPM 2.0, Secure Boot, and specific processor generations. For organizations still running older Intel or AMD hardware, full replacements—rather than upgrades—are frequently necessary.
ControlUp’s data that 19% of healthcare endpoints require replacement aligns with broader industry studies estimating that over 15-20% of business PCs globally do not meet Windows 11 requirements. While the mandate for modern security standards enhances baseline device safety, it forces costly refresh cycles, straining budgets in less-well-funded sectors.

Application Compatibility​

Another roadblock is business-critical software that is not certified or fully supported on Windows 11. In finance and healthcare, core systems—including patient management platforms and trading systems—may depend on legacy APIs or custom integrations. Testing, certification, and eventual migration of these systems often lag behind client OS upgrades, extending Windows 10 dependencies beyond hardware constraints.

Organizational Inertia and Change Management​

For larger organizations, even when technical readiness is achieved, the scale of communications, training, and staged rollouts adds friction. Employees require orientation on the new OS interface, policies must be updated, and help desk tickets increase during early rollout phases. Committees, risk reviews, and incremental deployment strategies add months to the process.

Security, Compliance, and Broader Risks​

The stakes of missing the migration deadline are high. After October 14, 2025, Microsoft will cease to provide regular security updates or technical support for Windows 10 outside of costly custom support agreements. This exposes organizations to:

• Heightened susceptibility to ransomware and malware, as attackers exploit unpatched vulnerabilities.
• Non-compliance with regulations mandating “supported and patched” software environments, risking fines or loss of certifications in sectors like healthcare, finance, and government.
• Increased operational costs as legacy systems demand bespoke maintenance, monitoring, and insurance.

Multinational organizations face added complexity due to staggered regional readiness, amplifying risks of security gaps and regulatory violations across borders.

Strengths Emerging from the Migration Surge​

Despite the challenges, the rapid progress tracked by ControlUp is not without its rewards for IT and business leaders:

Improved Baseline Security​

Windows 11 introduces stronger hardware and software security protocols—including virtualization-based security (VBS), hypervisor-protected code integrity, and enforced Secure Boot—all default on compliant hardware. Organizations completing migration benefit from reduced attack surfaces and alignment with modern cyber-insurance requirements.

Enhanced User Experience​

For sectors leading migration, feedback reports a more consistent and responsive user environment. Windows 11’s focus on streamlined UI and productivity-centric features (virtual desktops, integrated Teams, Snap Layouts) have shortened onboarding curves for new employees and boosted morale, especially in hybrid work settings.

Lifecycle Management Tools​

Enterprises leveraging endpoint management platforms like ControlUp, alongside Microsoft Endpoint Manager and others, are developing institutional expertise in large-scale OS migration. Automation, real-time analytics, and compliance dashboards reduce the manual labor and guesswork associated with legacy approaches.

Potential Pitfalls and Unresolved Questions​

Yet beneath these advances lurk unresolved risks deserving critical scrutiny:

Economic and Environmental Cost of Hardware Refreshes​

While migrating to Windows 11 may ultimately deliver long-term cost savings and security, the up-front expense of hardware replacement—not just in terms of capital expenditure but also IT labor, emissions, and e-waste—poses uncomfortable questions. Many enterprises in sectors like healthcare are forced to divert funds from other priorities to purchase new devices or rely on extended support contracts.

Unverified Claims and Data Limitations​

While ControlUp’s findings are based on a sample set exceeding one million endpoints—a robust cross-section—no singular assessment tool or vendor can guarantee visibility into all enterprise deployments. Some legacy, unmanaged, or niche verticals could be underrepresented. Cross-referencing with Gartner, IDC, and other market research firms is recommended for full market validation.
Additionally, claims on application compatibility and the precise financial impact of migration are less quantifiable without organization-specific data. Decision-makers should couple readiness tools with granular, internal risk assessments before deriving conclusions applicable to their environments.

Risk of Fragmented Environments​

If significant percentages of endpoints in particular regions or units—such as the Americas or healthcare—remain behind, organizations face the prospect of bifurcated environments: some devices modern and secure, others exposed and unsupported. This not only creates tech-support headaches but undermines the unified digital workplace strategies many enterprises seek.

Recommendations for Enterprises Navigating the Final Stretch​

With scarcely four months remaining until Microsoft halts Windows 10 updates, the following best practices emerge, drawn from ControlUp’s findings and wider industry guidance:

• Conduct a final, organization-wide readiness assessment using both third-party and built-in Microsoft tools to identify any lingering ineligible endpoints and prioritize replacements or upgrades.
• Establish clear, executive-empowered migration teams in large organizations, with authority to resolve cross-functional blockers and streamline procurement or communications.
• Emphasize regular communication and change management training for end-users, minimizing resistance and smoothing the experience curve.
• Negotiate with vendors for any extended support contracts needed, while mapping phase-out plans for legacy applications.
• Conduct post-migration security and compliance audits to ensure all devices align with both internal cyber standards and sectoral regulations.
• Plan responsibly for hardware recycling and sustainability to minimize e-waste and environmental impact associated with device refreshes.

Conclusion: The Urgency of the Final Mile​

The transition from Windows 10 to Windows 11 is not just a technological shift but a test of organizational resolve, resourcefulness, and risk management. ControlUp’s data marks clear progress, but the clock is rapidly ticking down on the grace period for action. The competitive edge and operational resilience of enterprises, particularly those in lagging sectors or geographies, will depend on their ability to marshal resources and expertise for a smooth migration.
As Microsoft’s support deadline grows ever closer, the next four months will be critical. Enterprises that navigate this pivot successfully will emerge on a foundation of improved security, performance, and regulatory posture. Those that miss the mark could find themselves contending with security vulnerabilities, compliance penalties, and growing costs—underscoring the value of sustained momentum and comprehensive planning on the path to Windows 11.

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Source: Global Banking | Finance | Review Half of Enterprise Windows Endpoints Have Not Yet Migrated to Windows 11, According to ControlUp Study