Windows 10 End of Support is Almost Here
As we move deeper into 2025, Windows 11 adoption is reaching a critical inflection point for enterprises worldwide. With Microsoft’s end-of-support deadline for Windows 10 set for October 14, 2025, IT leaders are accelerating their migration strategies. Of course, there are a number of complex variables to account for when modernizing, including workforce expectations and the ever-present challenge of legacy application compatibility.
In fact at the time of writing this article, Windows 11’s market share tracked by StatCounter reached 42.66% with predictions W11 adoption will surpass Windows 10 in the coming months.
The same report showed Windows 11’s market share at 26.19% 12 months ago.
The Push Toward Modernization
For many organizations, the shift to Windows 11 is not just an OS upgrade — it’s a catalyst for broader IT transformation. Windows 11 brings clear advantages: a more secure-by-design architecture, native support for modern hardware (with emphasis on TPM 2.0 and improved virtualization), and a refined employee experience aimed at hybrid work scenarios.
Many enterprises shifted their hardware refresh cycle to accommodate remote work needs in 2020 and are now reaching their natural point for another refresh making this an opportune time to embrace Windows 11 and make the most of their latest hardware investments. Of course, for certain organizations the move to Windows 11 on Copilot+ PCs may provide further incentive to modernize.
Yet, even as these benefits accumulate, adoption is far from automatic.
The Legacy Application Challenge
Legacy applications built for older environments don’t play nicely with Windows 11’s tightened security controls or new platform requirements, creating a major barrier to Windows 11 adoption.
For industries such as healthcare, manufacturing, and financial services – where custom-built, mission-critical software still runs on Windows 7 or 10 environments – migrating these apps requires careful planning. Compatibility testing, virtualization strategies, and (in some cases) costly redevelopment are all on the table.
Some organizations are leaning into solutions like:
- Application virtualization and containerization to isolate legacy applications from the host OS.
- Desktop-as-a-Service (DaaS) models to run legacy environments in the cloud, while frontline users leverage Windows 11 locally.
- Extended Security Updates (ESU) from Microsoft for Windows 10, to buy more time for complex migrations (though this is a stopgap, not a strategy).
The reality is that Windows 11’s stricter hardware requirements and security models can surface hidden technical debt. A major hurdle with the new requirements is that Windows 11 migration is the first 64-bit only Windows desktop which means enterprises with 16-bit applications must now find a path forward which can delay migration and lead to firms needlessly wasting money on ESUs. Enterprises that delayed modernization now face a compressed timeline.
What You Must Do When You Hit Compatibility Challenges
IT teams are leveraging tooling such as Microsoft’s App Assure and Test Base to validate compatibility before making the leap. While App Assure does provide a potential path forward for some applications, it is unlikely to provide a solution for other applications – particularly those containing 16-bit code and are no longer supported but are still critical to your organization. It can also take some time to get support and a direction forward. You will need a ready to use solution in-place while carrying out your migration. This can come in the form of application containers. Application containers provide a dedicated virtual file system and isolation techniques that can be leveraged to bring forward legacy application to modern operating systems.
Application containers equip organizations to confidently move forward with Windows 11 migrations without disrupting critical business operations.
Preparing for the Final Push
With the clock ticking toward the Windows 10 end-of-support deadline, proactive enterprises are adopting a phased, structured approach to transition:
- Inventory and Assessment: Cataloging devices, applications, and usage scenarios to build an accurate readiness picture.
- Prepare Applications: Revise and package applications as needed. Be sure to coordinate testing with subsets of each department as part of your rollout plan.
- User Segmentation: Identifying user personas and workload types to prioritize migrations.
- Training and Change Management: Ensuring that end-users are prepared for new workflows and experiences.
- Device Refresh Cycles: Aligning hardware refreshes with Windows 11 rollout to maximize performance gains.
- Ongoing Monitoring and Optimization: Using analytics to track adoption metrics and user sentiment post-migration.
The Road Ahead to Windows 11 Adoption
Windows 11 adoption in the enterprise is no longer a question of “if” but “how soon.” While the challenges of legacy application support are real and significant, they’re not insurmountable. Forward-thinking IT leaders are treating this transition as an opportunity to modernize infrastructure, enhance security, and empower a more productive workforce. These IT leaders will put their firm in the best possible position for future OS and desktop migrations by modernizing now.
In the coming months, expect to see a sharp uptick in enterprise migrations as organizations race to meet the Windows 10 sunset while building future-ready IT environments. For those that plan thoughtfully and act decisively, Windows 11 represents not just a technical upgrade, but a strategic advantage.
How to Securely Package Legacy Applications to Ensure Successful Windows 11 Adoption
To help establish your application modernization strategy for Windows 11, download our whitepaper How to Securely Run Legacy Applications on Windows 11 to explore how Cloudpaging enables you to lift and shift legacy applications to any modern physical or virtual Windows desktop without sacrificing functionality or performance:
