Windows 11 upgrade: The technical challenge is not the biggest hurdle

The bigger shift: Modern workplace management 

As my colleague Peter Horning points out, from an engineering perspective, moving from Windows 10 to 11 is by no means a massive undertaking. The real challenge is the necessary transition to modern workplace management and the potential need for application adjustments. In fact, this presents an ideal opportunity to embrace a broader cloud migration—though, of course, that’s easier said than done. 

While some companies have already transitioned from traditional on-premises setups to cloud-based workplace management using Intune and Azure solutions, they remain in the minority. At Cegeka, we see Windows 11 upgrades as a natural moment to integrate this transition. What’s surprising is how often organizations underestimate the shift to a new management model—more on that later.

A well-planned, thorough upgrade process 

Upgrading to Windows 11 isn’t an overwhelming task, but it’s not entirely plug-and-play either. While Windows 11 offers backward compatibility, applications don’t always function seamlessly post-upgrade. Issues can arise from outdated technologies or configurations—such as Edge Internet Explorer Mode settings or legacy authentication methods. To prevent disruptions like error messages or system crashes, a carefully planned and structured upgrade process is essential.

Key elements for a smooth transition 

The upgrade path to Windows 11 is largely familiar, but a few critical steps make all the difference: 

• Hardware compatibility check: Ensuring systems meet requirements like TPM 2.0, Secure Boot, and UEFI—especially important as acquiring new devices can take time. 

• Application readiness: Verifying compatibility with Windows 11 (and potentially Intune) and making necessary adjustments.  

• Phased rollout strategy: Following Microsoft’s best practice for "update rings," upgrading small user groups and select applications first to identify and resolve issues before scaling. 

• User adoption support: Depending on the client's needs, we provide user adoption support through manuals, apps, and floorwalkers. Our user adoption team can also assist with rollout planning and laptop distribution. Even after that, during the hypercare period, this team continues to offer support. 

Upgrade strategies and best practices

Will you opt for a phased rollout or a big bang upgrade to Windows 11? The right choice depends on your organization’s needs. A phased approach reduces disruption but requires managing both Windows 10 and Windows 11 in parallel. A big bang upgrade eliminates duplicate management by transitioning all systems at once, but it demands sufficient devices and meticulous planning.

Rolling out Windows 11 on new devices? We typically leverage Windows Autopilot pre-provisioning, especially when migrating to modern workplace management. Automated configuration ensures users are back to work within 30 minutes. For existing devices, we often recommend a clean installation, wiping old settings to prevent issues and enable seamless management via Intune. 

From traditional to modern workplace management

In modern workplace management, traditional tools like Microsoft Configuration Manager (formerly SCCM), Group Policies, and Active Directory are gradually being replaced—primarily by Intune for cloud-based device and application management. Entra ID (formerly Azure AD) plays a crucial role, enabling secure access through features like single sign-on and multi-factor authentication.

A key advantage of Intune is that the platform manages not only devices but also applications and user configurations. During the transition to modern management, standard configurations replace old OS images. Security settings, such as conditional access and device compliance, can be configured per user or device. 

With automated configurations and updates, management becomes simpler, faster, and more scalable. While some features are available on-prem, they are far more efficient and impactful in a cloud-based environment. 

Modern management: A different approach  

Transitioning to modern management brings significant changes—not just under the hood, but also in how IT teams approach management and security. Cloud-based authentication replaces traditional methods, file shares give way to OneDrive and SharePoint, and application deployment shifts from SCCM to centralized management with Intune. This shift is often underestimated by administrators. 

Getting there also comes with challenges. SCCM and Intune use different distribution formats, requiring legacy applications to be repackaged for compatibility. Thorough testing ensures these applications install and function correctly within the Intune environment. 

Post-transition, workstations are typically managed through the cloud, while certain systems and servers may remain on-prem. This hybrid setup adds complexity, as IT must balance different management and security approaches while maintaining two environments.

New knowledge, skills, and mindset 

The shift to modern security demands new expertise, different skills, and above all, a security-first mindset. Traditional Group Policies are being replaced by cloud-based security with Intune and conditional access—an approach that requires T-teams to think differently. Dynamic security becomes the standard, requiring continuous monitoring of users, devices, and data, while embedding zero trust principles into daily operations.

IT-teams must also reassess configurations, leveraging tools like Microsoft Security Baselines and attack surface reduction to proactively minimize risks.

A future-proof IT landscape 

Upgrading to Windows 11 is inevitable—but more importantly, it’s an opportunity to build a future-proof IT-environment. A tailored upgrade path, aligned with your organization's current state and future needs, ensures a seamless transition and lasting benefits.

We know the pitfalls and hidden gems 

With extensive experience from countless upgrade projects, we at Cegeka have a deep understanding of both the challenges and the opportunities in your journey. Whether it’s OS upgrades, modern workplace management transitions, or broader IT landscape modernization, we know how to navigate it all. From adjusting security settings and applications to lift-and-shift cloud migrations or even full digital transformations, we’ve done it.

Our experience shapes our upgrade approach, ensuring a smoother, more efficient process. What often sets us apart—especially during time-sensitive upgrades, migrations, transitions, and transformations—is our comprehensive service offering. We provide expert teams for everything from (technical) Windows 11 upgrades, managed workplace management, and setting up modern workplaces, to security, digital transformation, and, of course, our unique, dedicated user adoption team.