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The end of Windows 10 support has long been on the radar for IT leaders, and many organizations have acted accordingly. Through timely Windows 11 migrations or well-scoped Extended Security Update (ESU) plans, these teams have laid the groundwork for continuity, security, and compliance.

Yet broader endpoint data reveals a more mixed picture: a significant number of endpoints globally remain on Windows 10, and a snapshot of Lakeside’s customer community data from the last 30 days reveals that around 17% of Windows devices in enterprises are still running Windows 10,.

Chief Product Officer, Lakeside Software.

When the deadline approached, some IT teams face three core paths: upgrade, extend support, or repurpose. Those who have already completed the transition know that success depends on actionable insights, understanding how hardware, software, user experience, and system health intersect across the environment.

Drawing on enterprise implementations and endpoint telemetry, the following nine strategies offer a proven, data-driven approach which has already helped organizations make informed, efficient decisions as they exit Windows 10.

1. Use hardware and firmware data to assess upgrade readiness

Start by scanning each device’s firmware, CPU model, TPM presence, and memory availability. These indicators determine whether a machine is viable for Windows 11 or a candidate for alternative deployment.

Devices that fail Windows 11 checks may still be suitable for alternative deployments, such as thin client duties or alternative operating systems.

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2. Map application usage to target extended support investment

Microsoft ESUs allow the selective extension of Windows 10 security support. But blanket adoption is costly. Use software usage and dependency data to identify which systems truly require continued support, typically those running legacy, business-critical, or non-portable apps.

In a large government finance environment, usage analytics showed that only a small set of machines ran a critical reconciliation tool. That allowed ESU scope to be limited to those, while other units moved on.

3. Assess device health and digital experience, not just age

Device age alone is a blunt instrument. A lightly used older machine may outperform a newer but heavily burdened one. True insight comes from analysing metrics such as CPU load, memory pressure, disk latency, and digital employee experience (DEX) scores.

DEX scoring combines latency, responsiveness, error patterns, and resource contention to reveal where users struggle, often before issues surface as support tickets. This combined view helps IT teams categorize endpoints for upgrade, extended support, or decommissioning.

Devices with poor DEX scores may merit 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 high migration risk due to performance issues.

4. Track performance degradation over time

Upgrading to Windows 11 isn’t a fire-and-forget task. Ongoing feature and quality updates continually change how devices perform, making regular performance assessment essential.

Tracking trends in boot time, memory use, crash frequency, login delays, and latency helps identify machines that are starting to struggle—often the ones most likely to fail post-migration or during support extension.

5. Analyze software dependencies before changing platform

Application compatibility isn’t just about whether software launches; it’s also about what it depends on behind the scenes. Licensing constraints, authentication layers, middleware, and browser plugins can all prevent smooth transitions to Windows 11 or other platforms.

These issues often go unnoticed until workflows break or compliance risks emerge. Dependency mapping, based on real usage data, helps flag systems that rely on Windows-specific components or tightly coupled environments. Identifying them now reduces the chance of disruption and ensures that only suitable machines move forward.

6. Validate pilots with comparable data and usage feedback

Piloting new operating systems is more than a technical experiment. For pilots to be meaningful, monitoring must mirror the same telemetry used across your Windows domain. Performance, application responsiveness, resource stability and user feedback should be captured consistently.

Effective pilots also require anomaly detection, event correlation, and root cause analysis to ensure that feedback from test users can be traced to specific workload or compatibility issues. Without that depth, pilot success in limited settings may not hold under enterprise scale.

7. Investigate post-upgrade failures with device‑level diagnostics

Migrations sometimes complete but leave devices unstable. When systems underperform or fail after an upgrade, deep diagnostics are critical.

Whether the root cause is driver misalignment, firmware mismatch, resource contention, or configuration drift, only detailed device telemetry surfaces what changed and why.

This insight lets you refine driver packs, firmware baselines, and configuration policies, so that each successive wave improves.

8. Automate fixes for common migration blockers

Common issues such as full disks, outdated firmware, missing patches, or driver conflicts should be detected and resolved before migration attempts.

Automated remediation scripts or remote updates help precondition machines at scale. Organizations employing such practices report fewer support incidents and smoother deployment runs.

9. Weigh Windows 11 performance trade‑offs carefully

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

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

The bottom line

There is no one-size-fits-all exit from Windows 10. Some organizations will press ahead with Windows 11, others will extend support on key systems through Microsoft’s ESU offering, and still others will repurpose devices into alternative roles or platforms.

The common denominator across every path is visibility. With comprehensive, real-time insight into hardware, software usage, performance, and user experience, IT can make informed, intentional decisions instead of knee-jerk reactions.

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Chief Product Officer, Lakeside Software.