Enterprises Still Only Halfway to Windows 11 Switch

Simon Townsend
ControlUp

Microsoft's Windows 10 end of support is only several months away but new data shows enterprises still aren't feeling the urgency to migrate to Windows 11. The latest study data from ControlUp shows 50% of enterprise Windows endpoints still haven't completed Windows 11 migration. Although statistics indicate an improvement from last year's 82% of non-migrated endpoints, it suggests that enterprises will continue to incur expenses for Extended Security Updates (ESUs) to utilize Windows 10. The per user cost is expected to be $61 for year one, doubling to year two and rising to $244 year three.

Large enterprises may pay the steepest price for lagging on migration. ControlUp's analysis of more than one million endpoints indicates organizations with more than 10,000 Windows devices are at 42% migration. More complex IT environments, extensive legacy hardware and delays in assessments and planning are contributors.

There are a few bright lights in migration. ControlUp found technology (73%) and education sectors have already moved to Windows 11.

Getting to Windows 11

Lower adoption statistics point to the need to face legacy hardware issues earlier on, to avoid costly interim fixes like ESUs. Besides large enterprises, healthcare (41%) and finance (45%) also lag behind. Healthcare data shows 19% of endpoints need replacement to be able to run Windows 11. About 3% of finance endpoints will need replacement.

Although some sectors are yet to approach the 50% mark, the reality is many have migration-ready devices. The study indicates that 88% of enterprise Windows endpoint devices that are yet to migrate can support Windows 11. Another 1% will meet requirements with upgrades, and 11% need full replacement.

To encourage migration, Microsoft publishes useful documentation for a quick check on Windows 11 compatibility.  Organizations can use the PC Health Check app and be aware that, to migrate, devices must be running Windows 11, version 2004 or later.

For a thorough assessment into Windows 11 readiness, it's important to review, in detail, devices and software in use. Device battery health, whether the device can meet minimum requirements like 1 gigahertz (GHz) or faster speed, 4 gigabytes (GB) of RAM and 64 GB or more storage, and if the device already has TPM2.0 (Trusted Platform Module). All are elements that determine how easy a lift Windows 11 will be.

There is technology available now to help organizations more easily assess device readiness and accelerate migration. Enterprises with thousands of devices can leverage digital employee experience (DEX) tools that use automation to analyze Windows 11 device compatibility and software usage. These tools save IT considerable assessment time and flag underutilized applications that are adding to overall costs.

To support large scale migration, managed services providers (MSPs) and technology partners can help with device assessment. They can take the time burden off IT and deliver a ready-to-go migration strategy, then using their technical expertise, help IT manage the migration and solve issues related to device and application compatibility. Post migration they can provide insights into performance, and if needed, MSPs can continue to manage deployment.

The AI Question

AI-PCs are on the horizon, but at this point, enterprises should complete Windows 11 migration and make AI device capabilities a separate planning issue. Windows 11 offers security and application enhancements enterprises can benefit from now, while AI devices are still in the early adoption phase. If new devices are being purchased, it makes sense to determine if they are AI capable, to prepare for eventual applications.

No Time to Waste

Given that 88% of the non-migrated endpoint devices can support Windows 11, enterprises are encouraged to make the switch to gain Windows 11 benefits. They include support for Hyper-V, Firewall, Wi-Fi6, WPA3, and an encrypted DNS protocol, and support for more Bluetooth connections including Secure Simple Pairing, Secure Connections, and Core Spec compliance up through version 5.3. Another security enhancement is Smart App Control which vets apps before allowing them to be installed on a Windows 11 PC. Performance enhancements include Snap assist which helps multitasking by arranging open windows on one screen for easier viewing and remembering the layout; enhanced Microsoft Edge for better browsing speed, and seamless redocking in which Windows 11 remembers how you like things arranged when you connect to an external display or monitor, then reconnect later.

The long-term benefits of Windows 11 outweigh the expense of ESUs and through assessment tools and provider assists, enterprises can migrate more quickly, gaining both an economic and productivity advantage.

Simon Townsend is Head of the Office of the CTO at ControlUp

Related Links

The Latest

Escaping Pilot Purgatory: How AI Becomes an Operational Advantage

In live financial environments, capital markets software cannot pause for rebuilds. New capabilities are introduced as stacked technology layers to meet evolving demands while systems remain active, data keeps moving, and controls stay intact. AI is no exception, and its opportunities are significant: accelerated decision cycles, compressed manual workflows, and more effective operations across complex environments. The constraint isn't the models themselves, but the architectural environments they enter ...

Closing the Gap in Modern Tech and the Tools Meant to Monitor Them

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

MEAN TIME TO INSIGHT Podcast - Episode 23: NetOps Labor Shortage

In MEAN TIME TO INSIGHT Episode 23, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses the NetOps labor shortage ... 

Why FinOps Rewrote Its Mission and What It Signals for Technology Management

Technology management is evolving, and in turn, so is the scope of FinOps. The FinOps Foundation recently updated their mission statement from "advancing the people who manage the value of cloud" to "advancing the people who manage the value of technology." This seemingly small change solidifies a larger evolution: FinOps practitioners have organically expanded to be focused on more than just cloud cost optimization. Today, FinOps teams are largely — and quickly — expanding their job descriptions, evolving into a critical function for managing the full value of technology ...

Clearing the Path to AI: Why Vendor Consolidation Matters Now

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Cold Data, Hot Problem: Why AI Is Rewriting Enterprise Storage Strategy

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

Observability at a Crossroads: AI, Economics, Complexity and the Enduring Power of Open Source

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

Explainability Is the New Battleground in AI-Powered Observability

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

Empowering the Human Side of the Autonomous IT Age

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI Scale Is Outpacing Infrastructure - and IT Leaders Are Running Out of Time

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.

Enterprises Still Only Halfway to Windows 11 Switch

Simon Townsend
ControlUp

Microsoft's Windows 10 end of support is only several months away but new data shows enterprises still aren't feeling the urgency to migrate to Windows 11. The latest study data from ControlUp shows 50% of enterprise Windows endpoints still haven't completed Windows 11 migration. Although statistics indicate an improvement from last year's 82% of non-migrated endpoints, it suggests that enterprises will continue to incur expenses for Extended Security Updates (ESUs) to utilize Windows 10. The per user cost is expected to be $61 for year one, doubling to year two and rising to $244 year three.

Large enterprises may pay the steepest price for lagging on migration. ControlUp's analysis of more than one million endpoints indicates organizations with more than 10,000 Windows devices are at 42% migration. More complex IT environments, extensive legacy hardware and delays in assessments and planning are contributors.

There are a few bright lights in migration. ControlUp found technology (73%) and education sectors have already moved to Windows 11.

Getting to Windows 11

Lower adoption statistics point to the need to face legacy hardware issues earlier on, to avoid costly interim fixes like ESUs. Besides large enterprises, healthcare (41%) and finance (45%) also lag behind. Healthcare data shows 19% of endpoints need replacement to be able to run Windows 11. About 3% of finance endpoints will need replacement.

Although some sectors are yet to approach the 50% mark, the reality is many have migration-ready devices. The study indicates that 88% of enterprise Windows endpoint devices that are yet to migrate can support Windows 11. Another 1% will meet requirements with upgrades, and 11% need full replacement.

To encourage migration, Microsoft publishes useful documentation for a quick check on Windows 11 compatibility.  Organizations can use the PC Health Check app and be aware that, to migrate, devices must be running Windows 11, version 2004 or later.

For a thorough assessment into Windows 11 readiness, it's important to review, in detail, devices and software in use. Device battery health, whether the device can meet minimum requirements like 1 gigahertz (GHz) or faster speed, 4 gigabytes (GB) of RAM and 64 GB or more storage, and if the device already has TPM2.0 (Trusted Platform Module). All are elements that determine how easy a lift Windows 11 will be.

There is technology available now to help organizations more easily assess device readiness and accelerate migration. Enterprises with thousands of devices can leverage digital employee experience (DEX) tools that use automation to analyze Windows 11 device compatibility and software usage. These tools save IT considerable assessment time and flag underutilized applications that are adding to overall costs.

To support large scale migration, managed services providers (MSPs) and technology partners can help with device assessment. They can take the time burden off IT and deliver a ready-to-go migration strategy, then using their technical expertise, help IT manage the migration and solve issues related to device and application compatibility. Post migration they can provide insights into performance, and if needed, MSPs can continue to manage deployment.

The AI Question

AI-PCs are on the horizon, but at this point, enterprises should complete Windows 11 migration and make AI device capabilities a separate planning issue. Windows 11 offers security and application enhancements enterprises can benefit from now, while AI devices are still in the early adoption phase. If new devices are being purchased, it makes sense to determine if they are AI capable, to prepare for eventual applications.

No Time to Waste

Given that 88% of the non-migrated endpoint devices can support Windows 11, enterprises are encouraged to make the switch to gain Windows 11 benefits. They include support for Hyper-V, Firewall, Wi-Fi6, WPA3, and an encrypted DNS protocol, and support for more Bluetooth connections including Secure Simple Pairing, Secure Connections, and Core Spec compliance up through version 5.3. Another security enhancement is Smart App Control which vets apps before allowing them to be installed on a Windows 11 PC. Performance enhancements include Snap assist which helps multitasking by arranging open windows on one screen for easier viewing and remembering the layout; enhanced Microsoft Edge for better browsing speed, and seamless redocking in which Windows 11 remembers how you like things arranged when you connect to an external display or monitor, then reconnect later.

The long-term benefits of Windows 11 outweigh the expense of ESUs and through assessment tools and provider assists, enterprises can migrate more quickly, gaining both an economic and productivity advantage.

Simon Townsend is Head of the Office of the CTO at ControlUp

Related Links

The Latest

Escaping Pilot Purgatory: How AI Becomes an Operational Advantage

In live financial environments, capital markets software cannot pause for rebuilds. New capabilities are introduced as stacked technology layers to meet evolving demands while systems remain active, data keeps moving, and controls stay intact. AI is no exception, and its opportunities are significant: accelerated decision cycles, compressed manual workflows, and more effective operations across complex environments. The constraint isn't the models themselves, but the architectural environments they enter ...

Closing the Gap in Modern Tech and the Tools Meant to Monitor Them

Like most digital transformation shifts, organizations often prioritize productivity and leave security and observability to keep pace. This usually translates to both the mass implementation of new technology and fragmented monitoring and observability (M&O) tooling. In the era of AI and varied cloud architecture, a disparate observability function can be dangerous. IT teams will lack a complete picture of their IT environment, making it harder to diagnose issues while slowing down mean time to resolve (MTTR). In fact, according to recent data from the SolarWinds State of Monitoring & Observability Report, 77% of IT personnel said the lack of visibility across their on-prem and cloud architecture was an issue ...

MEAN TIME TO INSIGHT Podcast - Episode 23: NetOps Labor Shortage

In MEAN TIME TO INSIGHT Episode 23, Shamus McGillicuddy, VP of Research, Network Infrastructure and Operations, at EMA discusses the NetOps labor shortage ... 

Why FinOps Rewrote Its Mission and What It Signals for Technology Management

Technology management is evolving, and in turn, so is the scope of FinOps. The FinOps Foundation recently updated their mission statement from "advancing the people who manage the value of cloud" to "advancing the people who manage the value of technology." This seemingly small change solidifies a larger evolution: FinOps practitioners have organically expanded to be focused on more than just cloud cost optimization. Today, FinOps teams are largely — and quickly — expanding their job descriptions, evolving into a critical function for managing the full value of technology ...

Clearing the Path to AI: Why Vendor Consolidation Matters Now

Enterprises are under pressure to scale AI quickly. Yet despite considerable investment, adoption continues to stall. One of the most overlooked reasons is vendor sprawl ... In reality, no organization deliberately sets out to create sprawling vendor ecosystems. More often, complexity accumulates over time through well-intentioned initiatives, such as enterprise-wide digital transformation efforts, point solutions, or decentralized sourcing strategies ...

Cold Data, Hot Problem: Why AI Is Rewriting Enterprise Storage Strategy

Nearly every conversation about AI eventually circles back to compute. GPUs dominate the headlines while cloud platforms compete for workloads and model benchmarks drive investment decisions. But underneath that noise, a quieter infrastructure challenge is taking shape. The real bottleneck in enterprise AI is not processing power, it is the ability to store, manage and retrieve the relentless volumes of data that AI systems generate, consume and multiply ...

Observability at a Crossroads: AI, Economics, Complexity and the Enduring Power of Open Source

The 2026 Observability Survey from Grafana Labs paints a vivid picture of an industry maturing fast, where AI is welcomed with careful conditions, SaaS economics are reshaping spending decisions, complexity remains a defining challenge, and open standards continue to underpin it all ...

Explainability Is the New Battleground in AI-Powered Observability

The observability industry has an evolving relationship with AI. We're not skeptics, but it's clear that trust in AI must be earned ... In Grafana Labs' annual Observability Survey, 92% said they see real value in AI surfacing anomalies before they cause downtime. Another 91% endorsed AI for forecasting and root cause analysis. So while the demand is there, customers need it to be trustworthy, as the survey also found that the practitioners most enthusiastic about AI are also the most insistent on explainability ...

Empowering the Human Side of the Autonomous IT Age

In the modern enterprise, the conversation around AI has moved past skepticism toward a stage of active adoption. According to our 2026 State of IT Trends Report: The Human Side of Autonomous AI, nearly 90% of IT professionals view AI as a net positive, and this optimism is well-founded. We are seeing agentic AI move beyond simple automation to actively streamlining complex data insights and eliminating the manual toil that has long hindered innovation. However, as we integrate these autonomous agents into our ecosystems, the fundamental DNA of the IT role is evolving ...

AI Scale Is Outpacing Infrastructure - and IT Leaders Are Running Out of Time

AI workloads require an enormous amount of computing power ... What's also becoming abundantly clear is just how quickly AI's computing needs are leading to enterprise systems failure. According to Cockroach Labs' State of AI Infrastructure 2026 report, enterprise systems are much closer to failure than their organizations realize. The report ... suggests AI scale could cause widespread failures in as little as one year — making it a clear risk for business performance and reliability.