As the digital landscape constantly evolves, it's critical for businesses to stay ahead, especially when it comes to operating systems updates. A recent ControlUp study revealed that 82% of enterprise Windows endpoint devices have yet to migrate to Windows 11. With Microsoft's cutoff date on October 14, 2025, for Windows 10 support fast approaching, the urgency cannot be overstated. After the deadline, businesses will face steep costs for Microsoft's Extended Support Updates — starting at $61 per user in the first year, doubling the following year and soaring to $244 per unit annually by the third year.

Source: Microsoft

The stakes are high, not just financially but also in terms of security. The risks of neglecting system updates are evident from past incidents like the WannaCry malware outbreak and the breach at a Florida water treatment facility. Transitioning to Windows 11 will require not only software but also hardware upgrades, making the process more complex and critical than ever.

Hardware Hunting

Windows 11 requires specific device features and system requirements, including a 64-bit CPU, Secure Boot, and a TPM 2.0 chip, to ensure security and performance. Fortunately, the study indicates that 88% of the enterprise Windows endpoint devices that haven't migrated yet are ready for migration, 1% can be upgraded to meet requirements, and 11% need to be fully replaced.

Data and Software Migration

Migrating to a new operating system is a complex and costly task. It involves careful planning, test migrations, and user feedback, all while ensuring minimal downtime. Larger organizations might find themselves in this phase for an extended period. The migration journey encompasses three main stages: assessment, migration, and optimization.

1. Assessment: Before installing Windows 11, IT departments must assess their devices and software, given most organizations have heterogeneous computing environments and consider factors like hardware specifications, TPM2.0 chips, disk space, battery health, and the actual usage of deployed applications. Traditionally a manual process, this can now be automated with desktop monitoring tools, speeding up assessments and enabling informed migration decisions. This helps identify which devices are ready for Windows 11, which can be repurposed, and which need replacing. Additionally, it's an opportunity to review and consolidate software usage, potentially reducing costs by scaling down unnecessary licenses.

2. Migration: The actual migration typically involves using Microsoft Intune or technologies from Avanti to deploy the new OS, whether users are office-based or remote. Desktop monitoring tools add value by gathering user sentiment feedback through surveys, helping IT departments assess deployment success. Questions like "How did the migration go?" and "Were there any issues?" can guide further improvements. Additionally, these tools enable IT staff to remotely manage and control user desktops, allowing for quick issue resolution without the need for third-party tools.

3. Optimization: Even though upgrading to Windows 11 is free for organizations running Windows 10, there are hidden expenses like planning, app testing, and potential hardware upgrades. To maximize this investment, organizations should optimize their IT management by implementing digital employee experience tools during the Windows 11 rollout. This approach enhances visibility into IT performance, employee experience, and device functionality, allowing IT departments to be more proactive, reduce support tickets, and maintain better control over their computing environment.

In summary, upgrading to Windows 11 is more than just a software update — it's crucial for improving cybersecurity with better hardware. While the transition requires careful planning, following a structured migration process helps companies move smoothly while protecting their digital assets from growing threats.