Cloudiway AI Readiness Assessment is a platform that scans Microsoft 365 tenants to identify security risks, oversharing, and compliance gaps prior to deploying Microsoft 365 Copilot. The platform performs automated scans across Microsoft 365 workloads including Teams, SharePoint Online, OneDrive for Business, Exchange Online, Microsoft 365 Groups, Entra ID, and Microsoft Purview. It executes 100+ security checks organized across 19 risk categories, covering issues such as anonymous sharing links, dormant guest accounts, admin accounts without MFA, external mail forwarding, unlabeled sensitive files, and DLP policy gaps. Assessment results are expressed as a CAF Score (Cloud Adoption Framework), rated from 1.0 to 5.0, calculated across four weighted pillars: - Data Security (35%) - Governance (25%) - Compliance (25%) - Infrastructure (15%) A score of 4.5 or above indicates the environment is ready for Copilot deployment. The platform delivers an executive summary report and a technical report with detailed findings, along with a prioritized 30-day remediation roadmap. Scans are conducted using read-only delegated permissions; no tenant data is stored on Cloudiway servers. The platform is SOC 2 Type II and GDPR compliant. Cloudiway offers a white-label version of the platform for Managed Service Providers (MSPs), allowing partners to brand reports and deliver assessments under their own name. The first assessment is available at no cost.