Windows 365 Business or Enterprise? Field Notes From Early Cloud PC Deployments

Windows 365 launched in August 2021 with two editions that look similar on a pricing page and behave very differently in deployment. After extensive testing of both, we collected everything an MSP should know before the first customer asks: which edition fits, what it really costs, how long provisioning takes, and the errors waiting at the end. Treat this as a living document; we will keep adding to it as the product matures.

The Business vs Enterprise decision comes first#

Windows 365 Business is the lightweight path: license users and Cloud PCs provision in about 30 minutes. The simplicity has a price in control:

• No custom image deployment.
• Limited print options, because you do not control the network. Universal Print is not supported on the Business plan as of August 2021.
• Resizing is manual when you need more CPU or RAM, where Enterprise builds resizing natively into the interface. Resizing goes up only, never back down.
• Every user is created as a local admin on their Cloud PC by default, which is rarely what you want.
• A hybrid discount of around 16 percent applies when the base system runs Windows 10 Pro, which rules out devices like Chromebooks.
• Devices natively join Azure AD and enroll into Intune automatically, so you can push applications, compliance profiles, and scripts the moment the device provisions.

Enterprise is the heavier lift. Setup requires connecting to a local Active Directory environment; Microsoft says native Azure AD join support like the Business plan is on the way, but as of August 2021 it does not exist, and Azure AD Domain Services is not supported either. You still need an Azure subscription on top of the licensing so you can create a vNet with line of sight to the AD environment. In exchange, Enterprise supports custom images and has native resizing inside the Endpoint Manager admin center.

What the pricing really buys#

Between Business and Enterprise, plan costs are roughly the same. The full matrix is on Microsoft's pricing page (opens in new tab).

Compare roughly $30 per user per month against a similarly specced laptop over three years and the savings are not there. That is why we think the pitch to customers is flexibility and security, not cost. If cost savings is the actual goal, look at Azure Virtual Desktop instead: Nerdio published a strong comparison (opens in new tab) showing a 58 percent cost reduction versus Cloud PC when you pair reserved instances, pooled hosts, and auto-scaling.

Also worth knowing: which plans come with apps preinstalled. Those apps deploy automatically when the Cloud PC provisions and sign the user in, which is a genuinely nice experience for Teams and OneDrive in particular.

Provisioning times we actually measured#

Business: assign the licensing and wait. Our Cloud PC was ready at windows365.microsoft.com in about 30 minutes, sign-in worked immediately, and apps like Teams and OneDrive took roughly another 30 minutes to finish installing and signing in.

Enterprise: the prerequisites are where the time goes. Building from scratch, a domain controller, AD Connect with hybrid device sync, a vNet in Azure, and the connection in Endpoint Manager, took about 2 hours, plus another 30 minutes to provision the Cloud PC. Real environments with complex networking will take longer.

Patching on both plans#

Automated OS updates are built into both Business and Enterprise. If you want to control the patch cycle yourself, do it through Endpoint Manager or your RMM after deployment.

Why Intune is the natural management plane#

Because Business plans cannot use custom images, we strongly recommend adopting Intune if you have not already; otherwise you need another way to get the device under your RMM's management. At minimum, use Intune to deploy your RMM agent to the Cloud PC at first provision. Since the device integrates out of the box, it is also the right moment to push compliance policies, configuration profiles, and scripts directly from Endpoint Manager. Windows Information Protection (WIP) is an additional win here, keeping corporate data from being stored or shared to untrusted third parties such as a user's personal Google Drive.

The data loss scenarios nobody mentions#

Windows 365 gives users basic self-service management of their Cloud PC, including the ability to reset the device. A reset wipes any data on the device that is not syncing to OneDrive.

Business plans compound the risk because they lack native resize: moving up a size can mean a brand new Cloud PC, and again, anything not in OneDrive is gone. Deploy Known Folder Move through the Administrative Templates configuration profiles in Endpoint Manager so users' C drive folders back up to OneDrive automatically.

Errors you will hit, and what they actually mean#

On-premises network connection checks fail in Endpoint Manager#

Checks fail for plenty of reasons, but these three cover most cases:

1. Endpoint connectivity fails because there is no proper line of sight to the Active Directory environment. Confirm no firewall rules are blocking access and that the DNS servers in Azure are set to a custom IP.
2. AD sync is not configured for hybrid join, or is not syncing at least every 60 minutes. Confirm hybrid join is configured in the AD Connect wizard and there are no sync errors.
3. The AD user you entered cannot join computers to the domain. The error may blame a bad username or password, but it is most likely permissions. Confirm the account has the necessary rights on-premises.

The error below is typically a vNet configuration problem, no line of sight to the Active Directory environment:

And this final warning appears before your first Cloud PC provisions; it clears once a device successfully joins:

Defender prompts about Teams#

In our Enterprise deployment, end users saw this Microsoft Defender prompt:

Allowing access requires admin credentials. This article on managing Teams firewall requirements with Intune (opens in new tab) shows how to head that off in your deployments.

The resources worth bookmarking#

• Nerdio's Windows 365 vs AVD breakdown: getnerdio.com comparison (opens in new tab)
• Avoiding Defender errors with Teams: msendpointmgr.com guide (opens in new tab)
• Getting started with Windows 365 Business: Microsoft Tech Community (opens in new tab)
• Getting started with Windows 365 Enterprise: Microsoft Tech Community (opens in new tab)
• Plans and pricing: microsoft.com (opens in new tab)
• Troubleshooting the on-premises network connection: Microsoft Docs (opens in new tab)
• Official FAQ: microsoft.com (opens in new tab)