Upgrading to Windows 11 is more than a technical update—it’s a strategic opportunity to modernize your digital workplace. Many enterprises fell behind during Windows 10 due to the complexity of frequent updates, leaving legacy versions unsupported. It's the same story this year, with support for Win 10 ending in October 2025.
With Windows 11, planning your migration the right way can prevent those issues from recurring.
In this blog, we walk you through a 14-step Windows 11 migration plan designed specifically for enterprise IT teams managing large-scale environments.
📥 Download the Windows 11 Project Plan Template to kick-start your migration today.
Without clear structure and ownership, even the most well-intentioned IT migrations can lead to timeline delays, cost overruns, or poor end-user experiences. Windows 11 introduces new hardware requirements, updated security standards, and the opportunity to streamline legacy application estates. Whether you're running Windows 1809 or preparing for a more proactive upgrade, this plan outlines a framework to help you succeed.
Table of Contents:
- Step-by-step Windows 11 migration guide
- Plan the plan
- Define the project scope
- Build the project team
- Choose target infrastructure
- Design, build, test, manage "gold standard"
- Rationalize your application estate
- App testing & readiness
- Define your timelines
- Plan your scheduling methodology
- Agree end-user engagement plans
- Select the right tooling
- Plan deployment
- Reporting & dashboarding
- BAU handover & project closure
Start by aligning stakeholders, defining objectives, and identifying potential risks. Set expectations early and use a planning template to ensure your leadership team is aligned.
Establish what the end state looks like—including infrastructure, user groups, and compatibility targets. This prevents scope creep and keeps the project within time and budget.
Form a core migration team that includes BAU representatives. Focus your internal resources on decision-making and supplement execution with external specialists or automation tools.
Your platform needs to support secure, scalable OS delivery. Utilize our Windows 11 Assessment Service to assess your current readiness, identify potential blockers, and validate target environments.
Design a streamlined, secure "gold standard" with all required applications, drivers, and security policies. Testing this image against multiple deployment scenarios is key to project stability.
Reduce sprawl by identifying redundant or outdated apps. Tools like Juriba App Readiness help automate application normalization and categorization.
Run smoke tests on your in-scope apps using Juriba App Readiness. Automate testing and packaging to handle volume efficiently, especially for enterprises managing 1,000+ applications.
Map dependencies, automate workflows, and factor in readiness criteria. Prioritize quality and velocity, not just dates.
Define deployment rings, daily capacity, and resource allocation. Assign scheduling ownership and document fallback options.
Your migration success depends on the user experience. Use automated comms, feedback loops, and self-service portals to minimize resistance and maximize participation.
Integrate tools for inventory, workflow, packaging, deployment, and analytics. Consider building a central data warehouse for unified project visibility.
Align physical or virtual resources with scheduling and support capacity. For large or hybrid environments, define clear logistics ownership, especially if you’re engaging a service provider.
Automate dashboards that track migration velocity, app readiness, and user sentiment. This saves time and ensures visibility for leadership and project teams alike.
Plan your handoff carefully. Involve BAU teams early, share documentation, and use tooling that supports future Windows 11 servicing updates.
⚠️ Support for Windows 10 ends October 2025.
Download the Windows 11 Project Plan Template and move forward with confidence.