Strategic Windows 11 Migration at Enterprise Scale: How Anakage Empowered a Seamless, Automated Rollout

With Microsoft officially announcing the end of support for Windows 10 in October 2025, enterprises are now under pressure to initiate timely transitions to Windows 11. While the migration may appear to be a straightforward technical requirement, its implementation across distributed environments with thousands of endpoints presents logistical and operational complexities.

This article explores how a global organization with 5300 machines executed a successful, scalable Windows 11 migration by leveraging the Anakage platform and a custom PowerShell-based automation framework. The organization’s experience offers a model approach for IT executives seeking efficiency, transparency, and control during mass operating system transitions.

The Organizational Challenge

The enterprise faced several key constraints typical of large, distributed infrastructures:

• Multiple Sites and Custom Installers: The user base was distributed across various physical locations, with region-specific Windows 10 configurations and install media, making standardization difficult.

• Non-Privileged Users: End-users did not have local administrative rights, eliminating the possibility of self-managed upgrades.

• Resource and Time Constraints: Manual assessment of device compatibility and coordination of upgrades were time-consuming, resource-intensive, and prone to errors.

• Risk of Installation Failures: Without adequate user guidance, there was a significant risk that installation processes would be interrupted or aborted prematurely, leading to potential device instability.

Given the scale of the upgrade and the organization’s dependence on uninterrupted business continuity, the IT leadership team needed an intelligent automation solution that could manage pre-checks, deliver real-time progress visibility, and empower users with flexible scheduling—all without overburdening the IT service desk.

The Solution: Automated Migration Orchestrated by Anakage

To address the complexities, the enterprise adopted the Anakage platform to drive a user-aware, fully automated migration process. The solution was configured using a series of tightly integrated workflows and scripts designed to assess, notify, guide, and monitor the upgrade across the entire device estate.

1. Automated Campaign for Compatibility Assessment

The IT team initiated a system-wide Anakage campaign built around a custom PowerShell script. This script executed hardware and configuration checks to determine whether each machine met the minimum requirements for Windows 11—including CPU capability, TPM version, Secure Boot status, and available disk space.

The checks were performed silently in the background with no user disruption. Devices failing the criteria were flagged for IT review, while eligible machines progressed to the next stage of the campaign.

2. Intelligent Targeting Based on Location Groups

Users were logically grouped based on their geographic and organizational locations. Anakage leveraged this segmentation to ensure location-specific rollout strategies, including the appropriate Windows 11 media for each region.

This enabled regionally staggered deployments aligned with business hours, network readiness, and local IT support availability, thereby optimizing bandwidth consumption and reducing operational risk.

3. Flexible, User-Driven Scheduling via Snooze Options

Once a machine was confirmed as eligible, users received a prompt on their screens explaining the Windows 11 upgrade. The message included multiple snooze options such as:

• Remind me in 2 hours

• Schedule for tonight

• Schedule for the weekend

This approach empowered users to initiate the installation at their convenience while still aligning with enterprise-wide compliance deadlines. It also reduced user resistance and minimized productivity disruptions.

4. Real-Time Progress Visibility During Installation

A key feature of the Anakage implementation was the display of a dynamic progress bar throughout the installation process. Once a user initiated the upgrade, the custom PowerShell script triggered the migration while simultaneously engaging Anakage’s UI component to display real-time visual feedback.

This ensured that users remained informed and reduced the likelihood of them mistakenly closing or interrupting the installation—two of the most common causes of migration failures.

5. Centralized Reporting and Governance

Throughout the process, Anakage’s administrative console provided IT leadership with real-time analytics and actionable insights. Administrators had access to:

• Summary dashboards of successful and failed installations

• Detailed reports by location, department, or user group

• Diagnostic logs for failed or interrupted upgrades

• Trend analysis of user scheduling preferences

These reports enabled the IT team to course-correct in near real-time, proactively resolve issues, and demonstrate progress to executive stakeholders.

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Key Outcomes

Through the combined use of Anakage automation and custom scripting, the organization achieved significant results:

• Migration of thousands of eligible devices completed ahead of schedule

• Over 80% of users opted for self-scheduled upgrades, improving efficiency and adoption

• Incidents related to failed upgrades were reduced by over 70% compared to previous OS transitions

• Manual intervention by IT support staff was minimized, freeing up resources for higher-value initiatives

• Executive reporting dashboards provided clear visibility into progress and compliance

Conclusion: A Blueprint for Future-Ready Enterprise IT Operations

This Windows 11 migration initiative demonstrates how a modern, user-centric automation platform like Anakage can transform a traditionally complex and disruptive IT activity into a smooth, transparent, and scalable process.

By blending automation, scripting, and end-user flexibility, the organization was able to de-risk the upgrade, enhance operational control, and maintain business continuity throughout the transition.

For CIOs and IT Heads tasked with leading large-scale endpoint transformations, this case highlights the critical importance of selecting solutions that offer not only technical capability but also governance, insight, and adaptability.

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