With October 2025 set as the Microsoft deadline to end support for Windows 10, the urgency to migrate to Windows 11 is increasing. Post-deadline, Windows 10 will no longer receive critical security updates or new feature developments, exposing businesses to heightened security risks and operational inefficiencies.

VMblog sat down with Simon Townsend, Field CTO at ControlUp to discuss the state of Windows 11 migration in the enterprise. He shares insights on why companies should prepare their migration now, how to overcome migration barriers and the steps organizations should take to make their migration more seamless.

VMblog:  How many enterprise Windows devices have yet to transition to Windows 11?

Simon Townsend:  According to a recent ControlUp study, 82% of enterprise Windows endpoint devices are still operating on older versions of Windows, indicating a significant lag in migration efforts across industries. In particular, our data finds that finance organizations are the furthest behind in their migration status, with as many as 89%still needing to run Windows 11, even though they have the highest device readiness at 97%. Healthcare (80%) and general business (78%) categories also show high percentages of devices not yet migrated while their readiness is strong at 78% and 73% respectively. This shows that other factors, beyond device readiness, are likely at play.

VMblog:  Is migration status different in the Americas compared to Europe?

Townsend:  ControlUp's data shows that Europe is slightly ahead of the Americas in completed migrations. In Europe, 20% of enterprises have migrated, while 17% have migrated to Windows 11 in the Americas. This is despite the Americas having marginally more enterprise devices ready for migration, 88%, compared to 87% in Europe.

VMblog:  What are the financial implications of delaying the migration to Windows 11?

Townsend:  Delaying the migration to Windows 11 can be financially burdensome. Microsoft's Extended Support Updates for those remaining on Windows 10 start at $61 per user for the first year and rise to $244 per unit by the third year. These escalating costs underscore the financial impact of postponing the upgrade.

VMblog:  What hardware updates are required for Windows 11?

Townsend:  Windows 11 demands specific hardware features like a 64-bit CPU, Secure Boot, and TPM 2.0 chip, to enhance system security and performance. ControlUp's findings show that 12% of enterprise devices must be replaced to accommodate the new operating system. That leaves 88% of existing enterprise devices that are already hardware-ready for Windows 11, with just under 1% needing upgrades to meet the requirements to run Windows 11.

VMblog:  How important is software compatibility in the migration to Windows 11?

Townsend:  With a large portion of enterprise devices ready to accommodate Windows 11, software compatibility is likely creating a migration barrier. Ensuring software compatibility is crucial. All business-critical applications must run smoothly on Windows 11 to maintain productivity and avoid disruptions. Careful planning prior to migration is required and should include compatibility checks and necessary software updates to ensure a seamless transition.

VMblog:  What are the strategic steps recommended for migrating to Windows 11?

Townsend:  Given the complexities and high stakes associated with upgrading to Windows 11, strategic planning cannot be overstated. Starting early is crucial to manage the multifaceted process effectively. It's wise to take a proactive approach, using tools that simplify the readiness assessment and support a smooth transition. ControlUp Edge DX offers a built-in Windows 11 readiness assessment tool that can provide immediate insights into an organization's readiness state with a single click. This delivers complete visibility into data needed to develop an informed migration process. As a result, organizations can minimize downtime, mitigate risks, and ensure a successful upgrade.

VMblog:  What challenges do remote and hybrid work models pose for migrating to Windows 11?

Townsend:  The shift toward remote and hybrid work models adds complexity to the migration process, necessitating comprehensive strategies to ensure all employees, regardless of location, can smoothly transition to the new operating system. This might include hosting informational sessions, webinars, or distributing detailed digital checklists.

VMblog:  What long-term benefits does migrating to Windows 11 with a DEX solution offer?

Townsend:  Beyond the security updates, migrating to Windows 11 offers the chance to optimize the entire IT infrastructure, offer AI capabilities, and improve employee experience. Implementing digital employee experience (DEX) tools can both 1) improve IT performance visibility and elevate the user experience, driving additional operational efficiencies and reducing support tickets, and 2) help reduce the overall cost of managing Windows endpoints. With the right DEX solution, the number of IT admin, security, and remote management tools can be consolidated, simplifying management and reducing cost.

VMblog:  How does Windows 11 migration secure an organization's digital future?

Townsend:  Migrating to Windows 11 is crucial for organizations aiming to secure their digital futures in a rapidly evolving digital landscape. With careful planning and execution, companies can ensure their IT infrastructure is robust against emerging threats and aligned with modern operational needs so that they can better embrace new business priorities, securely, efficiently, and flexibly.

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