Oscar WhitmarshGuest blog: Solutions Engineer

Windows 11 Migration: The Enterprise Countdown Plan

Introduction

With support for Windows 10 ending on October 14, 2025, organisations face a race against time to migrate to Windows 11. Yet, many enterprise PCs still rely on the ageing OS. This delay, combined with fixed end-of-support dates, creates a strong sense of urgency for IT teams to act swiftly.

As a Solutions Engineer at ThreatAware, I have witnessed firsthand how IT departments are racing to upgrade thousands of devices before the deadline. Microsoft has made it clear that after the end-of-life date, Windows 10 will no longer receive free security updates. Continuing to run an unsupported OS not only exposes critical systems to cyber threats but may also violate compliance requirements in regulated industries. Enterprise organisations with 1,000 to 20,000 users simply cannot afford those risks—or the steep costs of extended support.

The Windows 11 migration is not just a routine upgrade: it’s a time-bound imperative for security and business continuity.

In the following sections I will discuss why this migration is so pressing, what challenges enterprises face, and how we can approach them with a solid plan and the right tools.

Providing Context

Migrating an entire device fleet to a new OS is one of the most complex projects enterprise IT teams face. With the Windows 10 end-of-life date fast approaching, the pressure is mounting for organisations to act now or risk running an obsolete platform. Recent industry studies have highlighted that a significant portion of enterprise devices remain on Windows 10, underscoring just how many organisations are behind schedule.

Key challenges include:

• Legacy Application Compatibility: Many organisations rely on legacy or custom applications built and tested on Windows 10 (or even older versions). Upgrading to Windows 11 raises concerns about whether these critical apps will function properly. This caution has led some companies to delay migrations until they are certain their mission-critical systems will operate without interruption.

• Hardware Requirements and Upgrades: Windows 11 has significantly more stringent hardware prerequisites than Windows 10. Microsoft now mandates a 64-bit CPU, UEFI Secure Boot, and a Trusted Platform Module (TPM) 2.0 chip, among other requirements. This means some older PCs, particularly those purchased before 2016, cannot run Windows 11 without hardware changes. For large organisations, identifying and addressing these gaps can involve a mix of minor fixes and full hardware replacements, both of which require careful planning and budgeting.

• Distributed Workforce & Device Visibility: Modern enterprises have a highly distributed IT estate—spanning multiple offices, remote workers, and devices that are not always connected to the corporate network. A common challenge is simply knowing the state of all devices. Incomplete or out-of-date inventory data can leave critical endpoints unaccounted for, creating blind spots that complicate compliance and planning efforts.

Together these factors illustrate why the Windows 11 migration is such a pressing issue. With the clock ticking, IT departments are under pressure to overcome compatibility roadblocks, ensure hardware readiness, and gain an accurate picture of their device landscape.

Process Overview For an enterprise migration involving thousands of users, a structured, phased strategy is essential. Here is a high-level overview of the process we follow:

1. Asset Discovery & Inventory: Start by gathering a comprehensive inventory of all user devices. Consolidate data from sources such as Active Directory, endpoint management systems, and any other available records. An accurate inventory is crucial—it is impossible to manage or upgrade what you have not identified.
2. Device Assessment (Compatibility Readiness): Assess each device’s readiness for Windows 11 by checking hardware and software compatibility. For hardware, verify that each machine meets the new requirements (e.g. TPM 2.0, Secure Boot, and sufficient resources). Simultaneously, review installed software for potential compatibility issues. The outcome is typically a categorisation of devices into groups that are ready, need minor adjustments, or require replacement.
3. Upgrade Planning & Readiness: With a clear view of the device landscape, plan the rollout. Decide on the method of deployment (in-place upgrade vs. re-imaging) and schedule the migration in phases or “waves”. Start with a pilot group to validate the process, then expand to larger groups while coordinating with various business units to minimise disruption.
4. Deployment & Tracking: Execute the Windows 11 deployments using enterprise-grade tools like Microsoft Endpoint Manager or Configuration Manager. Closely monitor the upgrade status with dashboards and reports. Track which devices have successfully transitioned, which need follow-up, and reconcile data across different systems to ensure accuracy.

Challenges and Hurdles Even with careful planning, enterprise migrations are rarely straightforward. Some common challenges include:

• Tracking Device Upgrade Status: Keeping an accurate record of which devices have been upgraded versus those still on Windows 10 can be difficult. Devices that are powered off or have been manually deferred can complicate the reporting process, making it challenging to maintain a clear view of the overall progress.

• Inconsistent Upgrade Reporting: Different tools may report different upgrade statuses. A device might appear upgraded in one system while still showing as pending in another. This inconsistency makes it hard for IT teams to gauge progress and resolve issues promptly.

• Identifying Hardware Limitations Early: Not every machine is Windows 11-capable. Some devices may have hidden hardware issues, such as outdated BIOS or missing firmware updates, which can prevent a successful upgrade. Accurate hardware data is essential to identify these limitations early and take corrective action.

• Lack of Centralised Visibility: In a large, distributed environment, asset data often exists in silos. Without a centralised view, it becomes challenging to get an accurate picture of the entire device fleet, potentially leaving some machines unnoticed until it’s too late.

Why Agentless Visibility Tools Matter

Given these complexities, robust visibility into IT assets is crucial. This is where an agentless cyber asset management platform like ThreatAware makes a significant difference. Here’s why:

• Consolidated Data Collection: Agentless tools pull data from multiple sources—Active Directory, endpoint management systems, cloud portals—and compile a unified inventory. This eliminates the need for time-consuming manual audits and ensures that no devices are missed, even in a distributed setup.

• Real-Time Device State and Cross-Verification: Continuous, automated data collection means you always have a current snapshot of your asset status. This real-time view allows IT teams to detect discrepancies early—such as devices that appear upgraded in one system but not another—and quickly address any issues.

• Deep Asset Intelligence: Beyond basic device details, agentless platforms provide granular information on hardware specifications, installed software, and even last-known online status. This depth of data is invaluable when determining which devices need hardware upgrades or software fixes before migrating to Windows 11.

• Enabling a Smooth Migration Workflow: By providing a consolidated, real-time dashboard of device status, agentless visibility tools support every stage of the migration process—from discovery to post-deployment validation. This “single source of truth” reduces uncertainty and ensures that IT teams can confidently manage the upgrade process, even in a large-scale, multi-department environment.

Lessons Learned and Best Practices

Having guided several enterprises through the Windows 10 to 11 migration, I would like to share some lessons learned and best practices that can benefit any organisation:

• Start Early and Plan Phases: Begin your migration well ahead of the end-of-support date. Break the project into phases, such as discovery, pilot, and deployment waves, with clear timelines. This approach provides a buffer for unforeseen issues.

• Conduct a Thorough Inventory Audit: Use automated discovery tools to compile an accurate inventory of all endpoints. Ensure that every device is accounted for and reconcile the data across all systems to prevent any gaps.

• Engage Stakeholders and Communicate: Treat the migration as a cross-functional project. Involve IT operations, application owners, security teams, and business unit leaders. Clear communication helps manage expectations and ensures that critical applications receive proper testing.

• Prioritise Compatibility Testing: Don’t assume that all applications will work flawlessly on Windows 11. Establish a testing environment to validate key applications and peripherals and ensure that any necessary patches or updates are applied well in advance.

• Address Hardware Gaps Proactively: Identify non-compliant devices early and decide on a remediation strategy. Sync hardware upgrades with your regular refresh cycles to avoid last-minute scrambles.

• Use Deployment Rings and Pilot Groups: Start with a pilot group to iron out kinks before rolling out the upgrade in larger waves. A phased approach minimises the impact of any issues and allows you to refine the process iteratively.

• Ensure Backups and a Rollback Plan: Protect user data by ensuring backups are in place and have a clear rollback plan ready if something goes wrong during the upgrade process.

• Leverage Tools for Monitoring and Visibility: Use dashboards and asset management platforms to maintain real-time visibility of your device fleet throughout the migration. This consolidation of data is key to confident decision-making and timely interventions.

Conclusion

Migrating from Windows 10 to Windows 11 in a large enterprise is undoubtedly challenging—but with the right approach, it is entirely achievable. By breaking the migration into manageable phases and addressing challenges such as tracking upgrade status, ensuring hardware compatibility, and maintaining centralised visibility, IT teams can mitigate risks and ensure a smoother transition.

In my experience, the use of an agentless cyber asset management platform like ThreatAware is a game changer. It transforms the migration process by providing comprehensive, real-time insights into your IT landscape, ensuring no device is left unaccounted for. With the deadline fast approaching, the key message is clear: act now. Start assessing your environment, plan your upgrades, and ensure you have the right tools in place to make a confident transition to Windows 11. The future of your enterprise’s security and operational efficiency depends on it.

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