Preparing for the End of Windows 10 Support: 9 Strategies for IT Teams

With the approaching end of Windows 10 support, this challenge has become a top priority for IT leaders. Many organizations have proactively taken steps. Through planned migration strategies to Windows 11 or targeted Extended Security Updates (ESU) plans, these teams have laid a strong foundation to ensure business continuity, cybersecurity, and regulatory compliance.

Microsoft plans to end free support for Windows 10 on October 14, 2025, meaning no free security updates or technical support will be available after this date. This necessitates quick decisions regarding upgrading or utilizing Extended Security Updates (ESU) programs to continue protecting systems. Source: Microsoft

However, broader endpoint data reveals a more mixed picture: a significant number of endpoints globally still run on Windows 10. A snapshot of Lakeside customer community data from the past thirty days indicates that approximately 17% of corporate Windows devices are still running Windows 10. This reflects a market still in transition, where some organizations are finalizing their strategies while others face the complexity of large-scale change.

As the Windows 10 support deadline approaches, IT teams have faced three primary paths: upgrading to Windows 11, extending support, or repurposing devices. Those who have already completed the transition understand that success hinges on actionable insights, comprehending how hardware, software, digital employee experience, and system health intertwine across the environment. Based on corporate applications and endpoint telemetry data, the following nine strategies offer a proven, data-driven approach that has already helped organizations make informed and effective decisions as they transition away from Windows 10:

Utilize Hardware and Firmware Data to Assess Windows 11 Upgrade Readiness

Start by scanning each device's firmware, CPU model, Trusted Platform Module (TPM) presence, and memory availability. These critical indicators determine whether a machine is compatible with Windows 11 or a candidate for an alternative deployment.

Hardware that fails Windows 11 compatibility tests may still be suitable for alternative deployments, such as thin client tasks or alternative operating systems.

Link Application Usage to Targeted Extended Support Investment (ESU)

Extended Security Updates (ESU) from Microsoft allow for the selective extension of Windows 10 security support. However, widespread adoption is costly. Use software usage and dependency data to identify systems that truly require ongoing support, typically those running legacy, business-critical, or non-portable applications.

The Extended Security Update (ESU) program provides critical and important security updates for up to three years after the official end-of-support date. Enrollment requires purchasing an annual license for each device. Source: Microsoft

In a large government financial environment, usage analytics showed that only a small subset of machines ran a critical reconciliation tool. This allowed ESU scope to be limited to those machines, while other units transitioned to Windows 11.

Evaluate Device Health and Digital Experience, Not Just Age

Device age alone is an inaccurate tool for assessing readiness. An older, lightly used machine may outperform a newer but overloaded one. True insight comes from analyzing metrics like CPU load, memory pressure, disk latency, and Digital Employee Experience (DEX) scores.

DEX scores combine latency, responsiveness, error patterns, and resource contention to reveal where users are struggling, often before issues appear as support tickets. This aggregated view helps IT teams categorize endpoints for upgrade, extended support, or decommissioning. Devices with poor DEX scores may warrant remediation, replacement, or exclusion from migration waves, even if they meet technical thresholds. In one public sector engagement, this approach identified frontline devices that, despite being newer, posed a high migration risk due to performance issues.

Track Performance Degradation Over Time

Upgrading to Windows 11 is not a "set it and forget it" task. Continuous feature and quality updates constantly change how hardware performs, making regular performance assessment essential. Tracking trends in boot time, memory usage, crash frequency, login delays, and latency helps identify machines that are beginning to struggle – often those most prone to failure post-migration or during extended support.

Analyze Software Dependencies Before Platform Change

Application compatibility isn't just about whether the software runs; it's also about what it relies on behind the scenes. Licensing restrictions, authentication layers, middleware, and browser plug-ins can prevent a smooth transition to Windows 11 or other platforms. These issues often go unnoticed until workflows break down or compliance risks emerge. Dependency mapping, based on real usage data, helps identify systems reliant on Windows-specific components or tightly integrated environments. Identifying them now reduces the chance of disruption and ensures that only the appropriate machines move forward.

Validate Pilot Projects with Comparable Data and Usage Feedback

Piloting new operating systems is more than just a technical exercise. For pilot projects to be meaningful, monitoring must reflect the same telemetry used across your Windows domain. Performance, application responsiveness, resource stability, and user feedback must be continuously captured. Effective pilot projects also require anomaly detection, event correlation, and root cause analysis to ensure feedback from pilot users can be traced to specific workload or compatibility issues. Without this depth, pilot success in limited settings may not hold up at an enterprise level.

Investigate Post-Upgrade Failures with Device-Level Diagnostics

Migrations are sometimes completed but leave devices unstable. When systems don't work well or fail after an upgrade, deep diagnostics are crucial. Whether the root cause is driver misalignment, outdated firmware, missing patches, or driver conflicts, only detailed device telemetry data reveals what changed and why. This insight allows you to optimize driver packages, firmware baselines, and configuration policies, so each successive wave improves.

Automate Fixes for Common Migration Blockers

Common issues like full disks, outdated firmware, missing patches, or driver conflicts should be detected and resolved before migration attempts. Automated remediation scripts or remote updates help prepare machines at scale. Organizations employing these practices report fewer support incidents and smoother deployments.

Carefully Balance Windows 11 Performance Trade-offs

Benchmark comparisons yield a mixed picture. In some of our anonymized global endpoint data, upgrading to Windows 11 correlates with approximately 7% better disk throughput and lower latency, but also 5% higher CPU utilization and 7% greater memory demand.

Although only about 12% of machines in this dataset had been migrated at the time, these metrics provide a realistic view of workload trade-offs. This suggests that older or lower-spec systems may require hardware upgrades or memory expansion to avoid performance regressions.

Conclusion

There is no one-size-fits-all solution for transitioning from Windows 10. Some organizations will continue to move forward with Windows 11, while others will extend support on key systems through Microsoft's ESU offering, and still others will repurpose hardware for alternative roles or platforms.

The common thread across every path is clear visibility. With comprehensive, real-time insights into hardware, software usage, performance, and user experience, IT can make informed and deliberate decisions rather than reactive ones.