Citrix to Windows 365: A Step-By-Step Migration Blueprint

14 August 2025
Cloud Migration
Written by George Dockrell

Citrix has long been the go-to for virtual desktops, but for IT teams seeking less overhead and more agility, Windows 365 is the natural next step. As a fast, scalable, and feature-rich Cloud PC platform, Windows 365 removes much of the complexity traditionally associated with VDI infrastructure.

Unlike legacy environments that demand constant hardware management, patch cycles, and intricate networking, Windows 365 simplifies deployment and day-to-day administration through native integration with Microsoft Entra ID, Microsoft Intune, and the broader Microsoft 365 ecosystem. With predictable pricing, built-in security, and full support for hybrid work models, it is quickly becoming the preferred platform for organizations looking to modernize and streamline their IT operations.

This blueprint gives IT professionals a clear, step-by-step guide to transitioning from Citrix to Windows 365. It covers everything from prerequisites and planning to provisioning, user onboarding, and key technical considerations to ensure a smooth and secure migration.

Why IT Teams Are Moving from Citrix to Windows 365?

As more organizations adopt cloud-first strategies, IT teams are re-evaluating how they deliver virtual desktops. Many are making the switch from Citrix to Microsoft’s native solutions, including Windows 365 and Azure Virtual Desktop, due to factors like cost, complexity, and better alignment with cloud initiatives. Below are some of the key drivers behind this transition:

Cost Efficiency for Microsoft-Centric Environments

Businesses already using Microsoft 365 or Azure can lower costs by moving to Microsoft’s virtualization platforms. Windows 365 eliminates the need for layered third-party licensing and reduces infrastructure overhead. It also simplifies operations and offers predictable per-user pricing, making budget planning easier.
Simplified Endpoint and Identity Management

Microsoft’s virtualization tools work seamlessly with widely adopted management platforms such as Microsoft Intune, Azure Portal, and Microsoft Entra ID. This eliminates the need for specialized Citrix expertise and enables administrators to manage users, devices, and policies from a single, familiar interface.
Built for the Cloud

Unlike legacy VDI platforms designed for on-premises environments, Windows 365 and Azure Virtual Desktop are built specifically for the cloud. They support scalable workloads, hybrid work models, and automated updates, reducing the need for continuous backend maintenance.
Reducing Complexity Through Vendor Consolidation

Transitioning to Microsoft as the sole virtualization provider helps streamline support, procurement, and system integration. It allows organizations to reduce vendor sprawl, simplify IT operations, and respond to issues more quickly by working within a unified technology ecosystem.

Citrix to Windows 365 Migration: A Strategic Overview

Before diving into the full technical workflow, it’s helpful to take a step back and understand the broader stages involved in migrating from Citrix to Windows 365. This high-level roadmap outlines the core phases IT teams typically follow when planning and executing the transition. While it doesn’t replace detailed guidance, it provides a clear framework for the journey ahead.

Start with a thorough assessment. Catalog your existing Citrix users, applications, and workflows. Pay particular attention to any dependencies tied to Citrix-specific configurations or policies.
Review licensing requirements. Examine your current Microsoft subscriptions and determine what is needed for Windows 365. Look for opportunities to consolidate resources or retire Citrix-related licenses where possible.
Run a pilot deployment. Choose a small, representative group of users to test Windows 365. This controlled rollout helps identify technical issues early and allows for adjustments before full deployment.
Proceed to production. Use feedback from the pilot to inform a broader migration plan. Gradually shift workloads to Windows 365 while phasing out Citrix infrastructure in a controlled manner.
Focus on continuous optimization. Use tools such as Azure Monitor, Endpoint Analytics, and Microsoft Intune to monitor performance, enhance user experience, and manage resources efficiently over time.

With a structured plan and phased approach, IT teams can carry out a smooth and secure migration from Citrix to Windows 365. The next section provides a detailed breakdown of each step in the process.

Breaking Down the Citrix-to-Windows 365 Migration Steps

Migrating from Citrix to Windows 365 involves more than just lifting and shifting virtual desktops. It requires a careful evaluation of infrastructure, licensing, identity, network, applications, and user readiness. This step-by-step guide simplifies that process, helping IT teams map out each major component of a successful transition.

Step 1: Choose the Right Windows 365 Edition

Start by selecting the edition that aligns with your organization’s structure:

Windows 365 Business is ideal for smaller deployments without complex infrastructure or hybrid identity requirements.
Windows 365 Enterprise supports deeper integration with existing Microsoft 365, Azure AD, and on-premises environments.

Your decision here will influence identity setup, network connectivity options, and endpoint management capabilities.

Step 2: Align Licensing and Azure Infrastructure

Select Windows 365 SKUs based on workload profiles and performance needs. Use group-based licensing to simplify license assignment at scale.

Enterprise deployments also require an active Azure subscription, particularly if hybrid networking or custom image hosting is involved.

Step 3: Configure Identity and Authentication

Determine whether to use Azure AD Join or Hybrid Azure AD Join:

Azure AD Join offers a streamlined, cloud-first approach supported in both editions.
Hybrid Join is suited for Enterprise environments needing on-premises Active Directory integration, but it adds complexity.

This step lays the groundwork for secure user access and policy enforcement.

Step 4: Set Up Network Connectivity

Enterprise environments may require secure access to internal resources. Configure:

VPN or ExpressRoute for seamless connectivity to on-premises networks.
RDP ShortPath to improve Cloud PC responsiveness, especially for users with limited bandwidth.

Business edition users rely on internet-based connectivity without custom routing.

Step 5: Choose the Operating System and Image Strategy

Select Windows 10 or Windows 11, depending on app compatibility and hardware requirements. Enterprise users can deploy:

Microsoft gallery images for simplicity.
Custom golden images to maintain consistency across user environments.

Custom images offer more control but require additional maintenance.

Step 6: Set Up Endpoint Management

Use Microsoft Endpoint Manager (Intune) to manage device configuration, enforce compliance, deploy apps, and set conditional access rules. This centralized approach is essential for Enterprise deployments and allows granular control over the Cloud PC environment.

Step 7: Sync User Identities to Azure AD

If not already in place, use Azure AD Connect to synchronize existing on-premises user accounts to Azure AD. This ensures users can authenticate to their Cloud PCs using familiar credentials and maintain access to Microsoft 365 resources.

Step 8: Prepare for User Adoption

Support a smooth transition by implementing a structured change management framework like ADKAR. Tailor user training to real-world scenarios to drive adoption and reduce support tickets.

Step 9: Deploy Applications

Applications can be delivered in multiple ways:

Manual install for simple setups.
Automated deployment via MEM, Windows Package Manager, or MSIX for scalability.
Third-party tools for niche or legacy apps.

Use golden images to pre-package core apps, but be mindful that this limits flexibility for updates.

Step 10: Migrate User Files and Folders

Shift user data from legacy file servers to modern cloud storage:

Use OneDrive, SharePoint, and Teams for accessibility and collaboration.
Microsoft Migration Manager and SharePoint tools streamline the transition.

This reduces local dependency and supports hybrid or remote work.

Step 11: Ensure Access to Corporate Services

Validate that essential backend services are reachable from Cloud PCs. This may involve network routing, DNS configuration, or port access to ensure uninterrupted service availability.

Step 12: Define the User Profile Strategy

Windows 365 uses persistent profiles, removing the need for FSLogix or roaming profiles. Optimize user experience with modern syncing methods:

Enterprise State Roaming
Edge and Office settings sync
OneDrive Known Folder Move (KFM) to back up key folders like Desktop, Documents, and Pictures

This ensures seamless user continuity and reduces dependency on legacy profile solutions.

Simplify Your Citrix to Windows 365 Migration with Apps4Rent

Migrating from Citrix to Windows 365 offers clear advantages such as reduced infrastructure complexity, simplified management, and a smoother experience for hybrid and remote users. However, a successful transition requires more than just changing platforms. Every part of the migration process, including identity setup, network configuration, application delivery, and user training, must be carefully aligned to maintain business continuity.

With proper planning and expert support, Windows 365 becomes a scalable and modern way to deliver cloud desktops without the burden of managing traditional VDI systems.

Apps4Rent has extensive experience guiding businesses through virtual desktop migrations. As a Microsoft Solutions Partner, we assist IT teams with every step of the process. From licensing evaluations and network design to Cloud PC deployment and user onboarding, we help ensure a smooth and secure migration. We also offer fully managed Windows 365 cloud desktops and Office 365 plans tailored to your business needs.

Contact Apps4Rent today to start your Citrix to Windows 365 migration with expert guidance and end-to-end support.