M365 Business Premium + M365 E5 Security = Windows 11 Enterprise?

Question

I'm trying to upgrade Windows devices from Windows Professional to Windows Enterprise so they can be used with features like Always On VPN, but they only seem to upgrade to Windows Business.

Licensing is through Microsoft 365 Business Premium subscriptions, assigned via a group, to which I've added Microsoft 365 E5 Security subscriptions. If I compare the product details of each subscription in the M365 Admin Centre, it seems to suggest Windows Enterprise is included with M365 E5 Security:

On a test laptop, which was purchased with an OEM licence for Windows 11 Professional, subscription activation only updates the licence to Windows 11 Business:

The Windows devices are hybrid Entra joined and prepared using Autopilot, which means two objects are listed in Entra ID for each machine: the initial, Entra joined instance, followed by the hybrid joined instance managed through Intune. Always On VPN connections work, but only if a connection is established manually.

Am I misinterpreting the version of Windows which is provided by M365 E5 Security, or are there other settings I need to check to verify why the licence isn't being upgraded to Enterprise? I've tried purchasing a separate Windows Enterprise E3 licence, but that doesn't get assigned successfully because the subscription plan conflicts with E5 Security.

If I look at the associated apps and services for the M365 E5 Security subscription in the admin centre, I don't see Windows Enterprise listed:

Is that a clearer indication that Windows Enterprise isn't included? In which case, which additional subscription would I need to purchase to acquire Windows Enterprise licences?

If anyone else has experienced similar challenges in upgrading to Enterprise, I'd really appreciate hearing if you found a solution!

Answer 1

Thank you for detail responding. 

I hope you understand that this issue falls under the scope of Windows licensing, which is outside the core support area I can directly assist with. 

At this point, I can only help by doing some research and sharing relevant resources. For your specific case, our Microsoft technical support will step in. 

A technical support technician can conduct a remote session to investigate the situation, review the backend configurations, and run the necessary synchronization tools to resolve the issue. If further intervention is required, they can refer the matter to a specialized team for in-depth analysis. 

I recommend raise a support ticket directly from the Microsoft 365 Admin Center. 

• Go to 365 Admin Center Portal
• You can raise a support ticket by going to the Support section> New Service Request. In description, you mention clearly your request.

Thank you for cooperation.

Warm regards, 
Tina L - MSFT | Microsoft Community Support Specialist

Answer 2

Thanks for your help and clarification on the licensing of Windows. I have purchased a separate Windows Enterprise E3 licence and am able to assign it to a test user account: I needed to use the "Manage apps & services" option for the existing M365 Business Premium licence so that the "Windows 10/11 Business" service was deselected.

However, on the corresponding test laptop I'm not seeing the licence status change: Windows is still reported as running Windows 11 Business. At this stage I don't know how to force the step-up to the Enterprise licence.

Here's a recap of the user and device details:

• User account is licensed with M365 Business Premium, M365 E5 Security, Windows Enterprise E3
• User account is added to the local Administrators group on the test laptop
• User account is temporarily excluded from all Conditional Access policies
• Laptop is running Windows 11 Professional, updated by subscription to Windows 11 Business
• Device is hybrid Entra joined, confirmed by checking with dsregcmd.exe:

• Windows Update runs without issue
• Laptop synchronises with Intune (via the Company Portal app) without issue
• Task Scheduler shows the LicenseAcquisition task runs successfully:

• Conditional Access policies that apply to users and target all resources (cloud apps) have an exclusion for the Windows Store for Business

I may try reimaging the laptop to see if that makes a difference, but I'm not 100% sure if that is likely to work or not.

Do you know if there is anything else I can check or try, other than the steps in the Microsoft document here:

https://learn.microsoft.com/en-us/windows/deployment/deploy-enterprise-licenses?pivots=windows-11#troubleshoot-the-user-experience

Answer 3

It’s been a while since I last heard from you — I just wanted to check in and see if you need any further assistance. Please feel free to let me know if there’s anything I can help with.

This forum has moved! 

< (Microsoft 365 and Office / Subscription, account, billing / For business / Subscription and billing) > is now supported on Microsoft Q&A. 

Starting July 16, new questions must be posted there.

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Looking forward to hearing from you!

Warm regards, 
Tina L - MSFT | Microsoft Community Support Specialist

Answer 4

Hello, 

Good day to you! 

Thank you for reaching out to Microsoft Community! 

For your situation, please take not this point to clarify why your devices are upgrading to Windows 11 Business instead of Windows 11 Enterprise: 

You're currently assigning: 

+ Microsoft 365 Business Premium 

This license includes rights to upgrade eligible devices to Windows 10/11 Business, but not Enterprise. It’s designed for small to medium-sized businesses and does not carry the Windows Enterprise entitlement. 

For reference: Upgrade Windows devices to Windows 10 or 11 Pro - Microsoft 365 Business Premium | Microsoft Learn 

+ Microsoft 365 E5 Security add-on: 

• Although Microsoft 365 E5 Security includes Enterprise-grade security features like Defender for Endpoint and Purview DLP, it does not include a Windows Enterprise license.
• This is a common misunderstanding; the term “Enterprise” in the feature list refers to security capabilities, not the Windows edition itself.
• Therefore, devices licensed with Business Premium + E5 Security will upgrade to Windows 11 Business, which is expected behavior based on the current licensing.

For this above reason, if you want to upgrade Windows 11 Enterprise, I suggest you 2 options: 

Option 1: Switch to Microsoft 365 E3 or E5 (full suite): 

These licenses include Windows Enterprise rights and will automatically upgrade eligible devices to Windows 11 Enterprisevia Subscription Activation. 

You need to meet some requirements:

• Devices must be running Windows 10/11 Pro
• Devices must be Azure AD joined, or Hybrid joined
• Licenses must be assigned to users in Microsoft 365 Admin Center

Option 2: Purchase Windows Enterprise E3/E5 standalone license:

If switching to M365 E3/E5 is not feasible, you can purchase a standalone Windows Enterprise license and assign it to users. 

**Note:**You should ensure there are no license conflicts with existing E5 Security plans. 

More detail information in this article: Windows subscription activation | Microsoft Learn 

Once again, thank you again for raising this issue; it’s helped broaden my understanding. I hope you understand that I want to help as much as I can within the scope of this forum.  

Feel free to reach out anytime if you need further assistance — we're always here to help. 

Best Regards,         

Tina L - MSFT | Microsoft Community Support Specialist