Is Your Organization Ready for Windows 365?

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 — M365 E3, E5, F3, or Business Premium; Windows 365 per-user SKU selection; 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 — co-management vs. cloud-only, Autopilot or Entra Join enrollment, compliance policy baseline
• Conditional Access policies — Named Location configuration, device compliance requirements, MFA enforcement for Cloud PC access
• Security baseline configuration — Microsoft Endpoint Security baseline applied, Defender for Endpoint integration, BitLocker policy for persistent OS disk
• 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 — SKU selection vs. workload profile, reserved vs. pay-as-you-go, Universal Print and storage add-ons

Get the Checklist

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<div class="form-group">
  <label for="checklist-name">Name <span style="color:#ef4444">*</span></label>
  <input type="text" id="checklist-name" name="name" required placeholder="Your full name">
</div>

<div class="form-group">
  <label for="checklist-email">Work Email <span style="color:#ef4444">*</span></label>
  <input type="email" id="checklist-email" name="email" required placeholder="you@company.com">
</div>

<div class="form-group">
  <label for="checklist-company">Company <span style="color:rgba(255,255,255,0.4);font-weight:400"> (optional)</span></label>
  <input type="text" id="checklist-company" name="company" placeholder="Your organization">
</div>

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