Office 365 ProPlus on Windows Server 2019

Mission Impossible?

How to Run Microsoft Office 365 ProPlus on Windows Server 2019

What now? It’s an obvious question when we read the decision by Microsoft: Office 365 ProPlus will no longer be supported on the new Windows Server 2019. But what are our options if we still want to use the latest technology? Our author Sabrina Rohenroth investigated the issue and came to the fortunate conclusion: It works after all!

Those of us who deal regularly with the Microsoft solutions can quickly come to the conclusion that certain decisions – whether they relate to licensing or technical issues – are not entirely logical, at least from a personal perspective. This is certainly the feeling you get when you take a closer look at the current discussion around Windows Server 2019 and Office 365 ProPlus. Because although your gut instinct tells you that the latest products will always offer the best compatibility and support, this example illustrates perfectly that Microsoft always has surprises up its sleeve.

What Exactly is the Problem?

The most important message first: Office 365 ProPlus will not be supported on Windows Server 2019.

This is made particularly clear in the system requirements for Office 365 ProPlus, in which Windows Server 2019 is not listed. And this is a problem for all customers who want to use the latest Windows Server 2019 to provision their Office 365 ProPlus remotely on the server.

Screenshot System Requirements for Office 365 ProPlus
Fig. 1: Screenshot System Requirements for Office 365 ProPlus, Source: Microsoft

But there’s another surprise tucked away in the system requirements for Office 365 ProPlus as well. Interested readers will note with astonishment that Office 365 ProPlus runs fine on older versions of Windows Server – although support on Windows Server 2016 will come to an end in October 2025. So the solution of provisioning Office 365 ProPlus in a virtual environment on Windows Server 2016 is a temporary stopgap at best.

It is important to mention in this context that the restriction is not due to the Click-2-Run installation method for Office 365 ProPlus. After all, Office 2019 has since been converted to this installation method as well – so the on-premises version of Office can definitely be provisioned on Windows Server 2019 in a virtualized setting.

Will it be Necessary to Switch to an Older Server Version?

A cursory glance at the system requirements for Office 365 ProPlus indicates that customers only have two ways of virtualizing Office and provisioning it in a remote environment:

  • A combination of the latest Windows Server version (2019) with Office 2019 on-premises, or
  • Provisioning Office 365 ProPlus on Windows Server 2016 or an older version.

So it appears that there is no way of running Office 365 on Windows Server 2019, initially at least. Switching to the Windows Server Semi-Annual-Channel (SAC) is not a solution, either, as the lack of Graphic User Interface (GUI) means that applications cannot be virtualized.

At Second Glance – It Works After All!

Naturally, the options outlined above are not completely satisfying for customers looking to combine cloud technologies with a modern server infrastructure in a hybrid environment.
The good news: There is another way of combining Office 365 ProPlus with Windows Server 2019. But it takes some adaptability – i.e. a workaround – that is again secluded away in the system requirements for Office 365 ProPlus.

Screenshot System Requirements for Office 365 ProPlus
Fig. 2: Screenshot System Requirements for Office 365 ProPlus, Source: Microsoft

While Windows Server 2019 is missing, the requirements do list the Windows operating system in a number of versions. So although it is not possible to virtualize Office 365 ProPlus directly on Windows Server 2019, there is certainly the option of using Windows Server 2019 to provision the Windows operating system – which in turn would support Office 365 ProPlus.

This means that Office 365 ProPlus can be combined with Windows Server 2019 by switching from a virtualized, remote application to a virtual desktop with a VDI environment.

The Azure service Windows Virtual Desktop – which will likely be available from 2019 – is another option, for the future at least. Put simply, it is a virtual desktop environment for Windows and Office that is made available as a managed service in Azure. Besides the benefits of a cloud service, it comes with another exciting feature, the Multi-User Windows 10 Experience that allows several users to ‘share’ one virtual desktop. Windows Virtual Desktop is optimized specifically to run with Office 365 ProPlus, which means that this service can also be used to provide a virtualized form of Office 365 ProPlus – albeit in the Microsoft Cloud.

Watch out for Licensing Traps

All of the provisioning options outlined above have technical and licensing consequences.

For instance, virtualization of Office 365 ProPlus within a virtual desktop requires not only an Office 365 ProPlus license and a RDS CAL, but also a Windows or VDA license – either with an active SA or an active subscription. Interested parties should exercise particular caution when dealing with licenses purchased via CSP, as the licenses that are available in this program only permit virtualization of the operating system on servers hosted in Azure.

A disadvantage currently associated with Windows Virtual Desktop is that the service is only available with Windows Enterprise licenses. At present, Windows Virtual Desktop does not have a solution for thin clients – which based on the momentary license conditions are only equipped with a VDA license. But the licensing requirements might certainly change, as the service will not be available until 2019.

It is certainly not compliant to provision Office 2019 on the server instead of Office 365 ProPlus – at least without purchasing Office on-premises licenses. It is essential to be particularly careful if the Microsoft 365 From SA license was purchased. Although it currently gives users access to Office Professional Plus, it only does so as a local copy for the licensed user – which means that provisioning on a terminal server is not compliant with the licensing terms.

So everyone currently planning a virtual rollout of Microsoft Office on Windows Server 2019 while keeping the option open to use Office 365 ProPlus would be well advised to remember the option of add-on licenses. They offer full rights of use for Office 2019 on-premises, with provisioning on terminal servers, as well as the right to provision Office 365 ProPlus. This ensures fully compliant use of all technical options associated with the virtualization of Windows Server 2019 in combination with Office.


All in all, the issue of Windows Server 2019 and Office 365 ProPlus proves that Microsoft will, from time to time, still leave people shaking their heads in disbelief. But although everything is heading inexorably for the cloud, workarounds and solutions continue to exist – currently at least – provided the users pay close attention to the stumbling blocks of licensing law.

  • User Productivity
  • Office

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