This guide presents an assessment for adopting a Windows in the Cloud solution, specifically utilizing Windows 365 and Azure Virtual Desktop. It outlines the process of building a detailed business case for the implementation of these technologies, which are designed to enhance productivity and optimize costs. The document details how organizations can align user personas with the respective product offerings of Windows 365 and Azure Virtual Desktop. It also describes the preparation of a cost-benefit analysis to identify potential growth and efficiency opportunities. Additionally, the guide defines a roadmap and outlines potential next steps for the adoption of the solution. The assessment aims to empower organizations to maximize their existing IT investments while ensuring flexibility and security in their virtual desktop environments.