Windows 11 has finally crossed a psychological and statistical threshold: adoption is accelerating across businesses and consumers, but the path to a full enterprise migration remains rocky as Windows 10’s end-of-support deadline (October 14, 2025) looms and Microsoft offers a costly — and temporary — Extended Security Updates (ESU) lifeline for organizations that can’t finish in time.
Enterprises have spent the past three years balancing the security and management advantages of Windows 11 against the realities of legacy hardware, bespoke applications, and regulatory constraints. Microsoft’s platform push, combined with Windows 11’s system requirements and new feature set, helped trigger an initial slow uptake. Over the past 12 months, that dynamic shifted: data shows Windows 11 now approaches parity with Windows 10 on desktops worldwide, while corporate readiness surveys reveal uneven migration progress across industries and regions.
Microsoft has also reopened a short-term escape hatch in the form of Extended Security Updates (ESU) for Windows 10 devices that remain on version 22H2. ESU provides critical and important security patches after end of servicing, but it is explicitly a stopgap — priced for commercial customers and structured to escalate annually — that pushes organizations to treat ESU as a contingency, not a strategy.
Readers and IT leaders should be cautious about relying on a single second-hand citation for key planning numbers; instead, use multiple telemetry sources (internal inventory, vendor readiness tools, and third-party market trackers) to build the migration picture relevant to their estates.
For IT leaders, the imperative is clear: prioritize inventory-driven, risk-based migrations; avoid complacency about ESU as a long-term fix; and invest in the tooling and partnerships that collapse timelines for remediation and testing. The coming months will reward organizations that execute purposeful plans — and penalize those that delay strategic migration decisions until after the deadline has passed.
Source: Redmondmag.com Windows 11 Adoption Gains Momentum as Windows 10 Support Sunset Looms -- Redmondmag.com
Background
Enterprises have spent the past three years balancing the security and management advantages of Windows 11 against the realities of legacy hardware, bespoke applications, and regulatory constraints. Microsoft’s platform push, combined with Windows 11’s system requirements and new feature set, helped trigger an initial slow uptake. Over the past 12 months, that dynamic shifted: data shows Windows 11 now approaches parity with Windows 10 on desktops worldwide, while corporate readiness surveys reveal uneven migration progress across industries and regions. Microsoft has also reopened a short-term escape hatch in the form of Extended Security Updates (ESU) for Windows 10 devices that remain on version 22H2. ESU provides critical and important security patches after end of servicing, but it is explicitly a stopgap — priced for commercial customers and structured to escalate annually — that pushes organizations to treat ESU as a contingency, not a strategy.
Current adoption and market share: what the numbers say
Short, verifiable facts:- Global desktop market share: As of September 2025, StatCounter’s worldwide desktop Windows version tracker shows Windows 11 at roughly 49.05% and Windows 10 at about 40.84%, with Windows 7 and other legacy versions making up the remainder. These figures indicate Windows 11 has edged ahead in aggregate share, but they also underline a sizable base of Windows 10 devices remaining in the field.
- Enterprise readiness snapshot: ControlUp’s Windows 11 Readiness analysis of more than one million enterprise endpoints reported that roughly half of enterprise-managed devices had not yet completed migration to Windows 11 as of its June 2025 report. Adoption in enterprise contexts is therefore improving — but far from universal, with sector and regional variance.
What enterprises are telling vendors: readiness, blockers, and surprises
ControlUp’s dataset — built into its Windows 11 Readiness Assessment and cited widely by industry outlets — highlights three core patterns:- Industry disparities: Education and technology sectors lead the migration, with many customers reporting migration rates well north of the enterprise average. Healthcare and finance lag considerably, driven by tightly validated applications, hardware constraints, and compliance requirements. ControlUp found that a meaningful proportion of healthcare endpoints simply need replacement before they can be upgraded.
- Regional differences: Europe generally outpaced the Americas in migration progress, with many European enterprises showing higher completion percentages. The Americas, particularly large multinational enterprises with sprawling device estates, demonstrate slower completion despite many devices being technically capable of running Windows 11. This suggests organizational policy, software testing, and change management — not just hardware — are throttling rollouts.
- Legacy oddities: Even in modern fleets, small numbers of truly legacy systems persist — older Windows 8.1 and even Windows 7 installations remain in pockets. These outliers raise compliance questions and increase the administrative and security burden on IT teams. ControlUp’s public commentary flagged legacy remnants and the management headaches they cause.
Microsoft’s ESU: mechanics, pricing, and limits
Microsoft’s Extended Security Updates program for Windows 10 is the official bridge for customers who cannot complete migration to Windows 11 by October 14, 2025. Key program points that organizations must accept:- Eligibility: ESU is available only for devices running Windows 10, version 22H2; devices on older Windows 10 feature updates are not eligible for ESU without first updating to 22H2. ESU enrolment is required to continue receiving critical and important security updates after end of servicing.
- Delivery & management: Updates for ESU-enrolled devices are delivered through Windows Update and can be managed via tools such as Microsoft Intune and Windows Autopatch. Microsoft has also built enrollment paths into Settings > Update & Security for consumer scenarios. For enterprise rollouts, Volume Licensing and CSP channels are supported.
- Pricing (commercial customers): Microsoft’s public guidance for commercial/volume-licensed customers sets Year One ESU pricing at $61 per device, with the price doubling in each subsequent year (e.g., Year Two $122, Year Three $244) — a rising cost profile designed to encourage migration rather than prolonged dependency. Microsoft and multiple industry outlets confirm this structure. Microsoft also offers discounts for cloud-managed deployments, and ESU is free for certain cloud-hosted Windows 10 instances (for example, Windows 365 and Azure Virtual Desktop).
- Consumer options: For consumers, Microsoft introduced a one-year ESU option and a $30-per-device path (or an opt-in via Microsoft Rewards) to receive updates through October 13, 2026. Regions in the EEA saw policy variations and temporary no-cost enrollment windows in some announcements; customers should confirm regional details for compliance.
The security calculus: risks, operational costs, and compliance implications
The decision to remain on Windows 10 with or without ESU is not binary; it’s an operational calculation that must weigh immediate continuity against medium-term risk and cost.- Short-term security: ESU covers critical and important vulnerabilities, reducing the risk of zero-day exposures that Microsoft patches under those severities. But ESU does not address non-security regressions or compatibility issues, and there is no guarantee new platform features or improved security telemetry will ever land on the older codebase. For high-risk environments (healthcare, finance, critical infrastructure), relying on ESU can be defensible but requires tightened compensating controls.
- Cost trajectory: The per-device cost model for ESU is deliberately punitive over time. The annual doubling of ESU fees is a nudge intended to force migration investments (inventory, remediation, application modernization, hardware refresh) rather than prolonged payment for legacy support. For organizations with tens or hundreds of thousands of endpoints, ESU can quickly become a budget sink.
- Compliance and regulatory risk: Many regulations require timely patching and vulnerability remediation. Using ESU does not exempt an organization from reporting or compliance obligations; it merely changes how patches are received. Some compliance frameworks or insurers may treat reliance on ESU as increased residual risk, potentially affecting audit outcomes or insurance premiums. This is a non-trivial consideration for regulated sectors.
- Operational complexity: Maintaining two parallel platforms at scale — a modern Windows 11 fleet and a Windows 10+ESU fleet — multiplies management overhead. Inventory reconciliation, update testing, configuration baselines, driver compatibility matrices, and endpoint security policies all become more complex. Organizations without mature endpoint management pipelines will see disproportionate friction.
Migration playbook: practical steps IT leaders should prioritize now
Organizations that still face migration work should treat the next months as a sprint and adopt a disciplined, risk-based migration strategy. A practical playbook includes:- Inventory and segmentation. Run a full hardware and software inventory, tagging devices by upgradeability, application compatibility, and business criticality. Prioritize mission-critical systems and those with regulatory exposure.
- Use readiness tooling. Deploy assessments such as ControlUp’s Readiness Assessment or vendor equivalents to identify devices that need remediation, driver updates, or full hardware replacement. These tools speed discovery and provide data-driven budgets.
- Create a phased migration plan. Move non-critical, easily-upgradable devices first to build momentum; then address complex application owners, test groups, and regulated units with staged pilots. Ensure rollback plans are well-documented.
- Leverage cloud & management discounts. If eligible, consider Intune or Windows Autopatch for discounted ESU pricing and to simplify deployment. Cloud-hosted Windows 10 instances may be eligible for different ESU treatments, which can change the economics for certain workloads.
- Communicate and train. Coordinate with application owners, security/compliance teams, and procurement to ensure firmware, driver support, and third-party vendor compatibility are validated ahead of mass rollouts.
The hardware reality: who needs replacement, and why it matters
A central reason Windows 11 adoption in enterprises is slower than Windows 10’s initial migration is the hardware bar. Windows 11 requires modern CPU features, firmware (UEFI Secure Boot), TPM 2.0 by default, and other platform security features. While Microsoft's hardware-probe tooling and compatibility checks have improved, many organizations find:- A portion of their fleet simply cannot be upgraded. Some commodity endpoints lack TPM 2.0 or have CPU families that fail Microsoft’s compatibility criteria. These devices either require hardware replacement or creative alternatives (cloud PCs, Windows 365) to support a modern platform without replacing physical hardware.
- Application and driver lifecycles matter. Even when a device meets hardware requirements, critical line-of-business apps may not have been certified for Windows 11, or vendor driver support is lacking. That often creates multi-month remediation projects involving ISVs, internal QA, and staged deployments.
- The environmental and procurement angle. Large-scale hardware refreshes require capital planning, recycling strategies, and endpoint disposal — real-world constraints that cannot be solved by a simple OS upgrade button. These realities increase the friction of rapid migrations.
Vendor and partner landscape: how the market is responding
The last months have seen ecosystem responses aimed at reducing migration friction:- Third-party remediation and compatibility tools — vendors offer application compatibility shims, driver validation platforms, and automated remediation scripts to cut testing time.
- Cloud PC and virtualization solutions — Windows 365 and Azure Virtual Desktop provide an alternative to physical replacement in some use-cases by delivering Windows 11-capable virtual desktops to older endpoints.
- Managed service offers — partners are packaging migration services: discovery, pilot, imaging, user training, and post-migration support as bundled engagements to accelerate timeline and reduce internal resource strain.
Fact-checking note and unverifiable claims
The recent coverage includes a claim attributed to a June Microsoft report that “over 53 percent of enterprise-managed Windows devices still run Windows 10 version 22H2.” Careful searches of Microsoft’s June 2025 documentation and public blogs did not surface a Microsoft-published report with that precise language and percentage in the public corpus available at the time of reporting. Where possible, the summary and figures in this piece are corroborated using StatCounter’s OS version tracker and ControlUp’s enterprise report; the specific Microsoft June report reference could not be located and therefore should be treated as unverified until the original Microsoft publication is produced or identified.Readers and IT leaders should be cautious about relying on a single second-hand citation for key planning numbers; instead, use multiple telemetry sources (internal inventory, vendor readiness tools, and third-party market trackers) to build the migration picture relevant to their estates.
Strategic implications for CIOs and security leaders
This transition period is a test of operational maturity for many IT organizations. The few most important strategic implications:- Treat ESU as tactical insurance, not a strategic direction. ESU reduces immediate exposure to critical vulnerabilities but introduces a multi-year, escalating operating cost. Use ESU where necessary, but pair it with a measurable migration roadmap and budget.
- Plan for a dual-mode endpoint estate in the short-term. Organizations should assume they’ll run both Windows 10 (ESU-covered) and Windows 11 concurrently for months and develop coherent management and monitoring strategies for both. This reduces surprise operational costs.
- Prioritize high-risk and regulated workloads. If resources are limited, begin migrations with compliance-first systems (healthcare, finance) where the regulatory and security stakes are highest.
- Consider alternative delivery models. For workstations that cannot be economically replaced, virtual desktop infrastructure or Windows 365 Cloud PCs can deliver Windows 11 benefits without physical refresh — but evaluate networking, licensing, and user experience trade-offs.
- Embed migration into broader IT modernization. Where possible, couple OS migration with application rationalization, desktop-as-a-service assessments, and endpoint security upgrades (EDR, EDR-XDR integrations) to capture long-term value from the project.
What to watch next
- ESU enrollment rollout and regional policy clarifications. Microsoft’s consumer and region-specific treatments for ESU have evolved; IT teams should monitor Microsoft’s official guidance and Intune/Autopatch documentation for enrollment windows and eligibility details.
- Ecosystem pricing and partner discounts. Watch for CSP and volume-licensing channel updates that may alter ESU economics (cloud discounts via Intune/Windows Autopatch are notable).
- Migration tooling maturity. Tools that accelerate compatibility testing, automated remediation, and large-scale imaging will materially reduce migration time for large organizations; early pilots are a good investment.
- Regulatory responses. Regulators or sector-specific authorities may weigh in on acceptable remediation approaches for critical systems running end-of-life OS versions; compliance teams should watch guidance closely.
Conclusion
Windows 11 adoption is gaining momentum, and the platform has overtaken Windows 10 in aggregate desktop share — a milestone that signals broad movement across consumers and many businesses. Yet enterprise migration remains a complex, uneven process. Legacy hardware, application compatibility, procurement cycles, and regulatory constraints mean many organizations will enter the post–Windows 10 era with a mixed estate. Microsoft’s ESU program provides a short-term safety net, but its cost structure and limitations make it a tactical rather than strategic option.For IT leaders, the imperative is clear: prioritize inventory-driven, risk-based migrations; avoid complacency about ESU as a long-term fix; and invest in the tooling and partnerships that collapse timelines for remediation and testing. The coming months will reward organizations that execute purposeful plans — and penalize those that delay strategic migration decisions until after the deadline has passed.
Source: Redmondmag.com Windows 11 Adoption Gains Momentum as Windows 10 Support Sunset Looms -- Redmondmag.com
