Ever since Apple began rolling out Macs using its own Arm chips just over two years ago, Microsoft officials have provided incomplete answers to users' questions about running Windows on those devices. But today, February 16, Microsoft added a new support page which (possibly) added a bit more official guidance for those interested in using Windows 11 on M1 and M2 Macs.

Traditionally, those interested in running Windows on a Mac would run Windows directly on Apple hardware using Apple Boot Camp or run Windows via third-party virtualization software like Parallels Desktop, VMware or Oracle VirtualBox. Microsoft officials have said that customers could license a Windows 11 virtual machine on an Apple Silicon Mac using a retail license, but Microsoft might or might not support them if they encountered compatibility issues. Microsoft officials have continued to stress that Windows on Arm (WoA) was built to run on certain Qualcomm Arm processors only.

In Microsoft's new support article, officials stated that there are two ways to use Windows with Mac: Microsoft's Windows 365 Cloud PC service or Parallels Desktop 18, which supports running the Arm versions of Windows 11 Pro and Windows 11 Enterprise virtually. The article notes there are limitations in running Windows 11 on Arm, including incompatibility with apps using DirectX 12 or OpenGL3.3 or higher, as well as with apps requiring nested virtualization, such as apps requiring the Windows Subsystem for Android, Windows Subsystem for Linux, Windows Sandbox and Virtualization-based Security (VBS).

Parallels has been touting the ability of its virtualization software to run Windows 11 on Arm on Apple Silicon-based Macs for a while now. But now it is "authorized" to do so, whatever that distinction actually means.

There is no mention in the new Microsoft support article about support for running Windows 11 on Apple Silicon hardware via Azure Virtual Desktop, VMware or Oracle. I asked Microsoft why these scenarios are not called out. I also asked why Microsoft published this new support page guidance today. So far, no word back on either query.

Update (February 17): A spokesperson sent the following statement, which circumvented the questions I asked: "It’s important to ensure customers have the right information to make informed decisions about the technology they use. Customers have asked what their options are for running Windows 11 with Apple Mac computers with M1 and M2 chips, so Microsoft published a support page detailing the options that are authorized." The spokesperson said Microsoft had "nothing to share at this time" on any of the questions I asked.

"While it’s good to see Microsoft offering some semi-officially guidance, the omission of certain technologies leaves it incomplete," said Directions on Microsoft analyst Wes Miller. "I also notice this still does not mention support or supportability of the software when running directly on Apple silicon. Customers need to continue to bear that in mind if they’re relying on a Windows VM on an Apple silicon Mac for business-critical work."

Microsoft is targeting June 2023 as its delivery date for a new Windows 365 offering called "Windows 365 Frontline." Microsoft posted a note about Windows 365 Frontline on its Microsoft 365 Roadmap site on February 10, stating it would be available worldwide for PC, Mac, mobile and web users.

Microsoft made its Windows 365/Cloud PC service generally available in 2021. Windows 365 is a cloud-based virtualization service that builds on top of and complements Azure Virtual Desktop. Windows 365 is for business users only at this point and costs anywhere from $20 to $162 per user per month based on cores, RAM and storage.

Frontline workers (sometimes also called "firstline workers") are "deskless" workers who are employed on the front lines in retail, healthcare, hospitality and other industries and are a big target for Microsoft’s subscription-based Microsoft 365 services. Microsoft officials claimed early last year that there were two billion frontline workers worldwide, representing 80% of the global workforce. Microsoft officials said they'd seen 400% growth (from some undisclosed number) in monthly active usage of its Teams platform among frontline workers since the start of the COVID-19 pandemic from March 2020 to November 2021.

The exact form the coming Windows 365 Frontline offering will take isn't explained in the roadmap entry. Will it be a new edition which will sit alongside the current Windows 365 Business and Enterprise variants? Will it be available as an add-on to Microsoft 365 subscribers? How much will it cost? I asked Microsoft, but a spokesperson would only say that Microsoft had "nothing to share at this time" about its own new roadmap entry.

The Windows 365 Frontline entry notes that the coming release is "designed for organizations to provide Cloud PCs for shift workers or part time workers that only need a Cloud PC for a limited amount of time each day or week."

My assumption is Windows 365 Frontline will be built on the "Windows 365 Boot" capability that Microsoft officials discussed in April 2022. Officials said this coming boot-to-cloud functionality would be better than initially booting Windows locally and then connecting to the cloud because it would allow users to pick up exactly where they were last time they logged in with Windows 365. They said that the boot-to-cloud feature would be configurable by admins using Endpoint Manager. And they described this feature as "a great option for frontline workers using shared devices."

The Windows 365 Frontline offering could also come with limited hours of availability, such as pool of hours the Cloud PC could be used in a given week, which could be more appropriate for a shift worker than salary-based “knowledge worker." This might give Microsoft an option to add a lower-priced Windows 365 line-up to its roster.

Windows 365 Boot was one of four new Windows 365 capabilities that company officials touted last year as examples of tight Windows and Cloud PC integrations.

Microsoft also announced and delivered the Windows 365 App which enables users to pin their customized Cloud Desktop apps to their Windows 11 taskbar and/or Start menu for easy access. They also talked up "Windows 365 Switch," which will allow users to move between their Cloud PCs and their local desktop just as easily as they currently can move between different desktops using the Task Switcher; and "Windows 365 Offline," which will allow users to work in their Cloud PCs even when disconnected from the Internet. They'll be able to reconnect and sync later without data loss, officials said. Microsoft hasn't provided any delivery timing for Boot, Switch or Offline, but these capabilities are likely to be delivered with a Windows 11 feature update (or maybe as one of its interim update "moments" before this fall) as these features require tight integration with the OS.