Most Windows 365 deployments that stall or fail do so for the same predictable reasons — prerequisites that were skipped, not unknown technical problems. This checklist gives you a structured way to confirm you have the foundations in place before your first Cloud PC goes live.
What the Checklist Covers
Walk through each area before you provision a single Cloud PC:
- Licensing prerequisites — Windows E3, Intune, and Entra ID P1 base entitlements (typically via Microsoft 365 E3, E5, or F3); Windows 365 Enterprise vs. Flex; license assignment approach
- Azure AD / Entra ID requirements — tenant configuration, Hybrid Entra Join vs. Entra Join decision, UPN suffix alignment
- Network readiness — bandwidth per concurrent session, latency to target Azure regions, split tunneling for VPN users, RDP Shortpath configuration
- Intune enrollment prerequisites — enrollment restrictions, co-management vs. cloud-only, Autopilot device preparation, Cloud PC compliance policy
- Conditional Access policies — Named Location configuration, device compliance requirements, MFA enforcement for Cloud PC access
- Security baseline configuration — Windows 365 security baseline piloted, Defender for Endpoint integration, Cloud PC disk encryption and compliance settings
- User provisioning workflow — group-based licensing, provisioning policy targeting, grace period and reprovisioning decisions
- Image management decisions — Microsoft-hosted gallery image vs. custom image, patching strategy, image version control process
- Monitoring and support setup — Cloud PC health dashboard, connectivity health checks, support escalation path for end users
- Cost estimation worksheet — Cloud PC size vs. workload profile, entitlements you already own, disaster recovery, Universal Print, and storage add-ons
Get the Checklist
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