Hands-On with Windows 365 on Mac, Chromebook, and iPad

Posted on August 3, 2021 by Paul Thurrott in Uncategorized with 17 Comments

Yesterday, I looked at the experience of using Windows 365 on Windows 10/11 using the Remote Desktop app. But what about other platforms like Mac, Chromebook, and iPad?

Each presents its own challenges, but it’s interesting to note that Microsoft makes a native Remote Desktop client on Mac and iPad (and on Android), while Chromebook users will typically access the service via the web client. So in the spirit of my earlier mile-high examination of Windows 365, here’s what it’s like to access this service on these other platforms.


To get started with Windows 365, I downloaded and installed Microsoft Remote Desktop from the Mac Store. Similar to the Windows version, you then need to get a subscription URL from the Windows 365 website. Then, open Remote Desktop, choose Workspace > Add Workspace, paste in the subscription URL, authenticate, and then add your Cloud PC to the app. When all that is done, the Cloud PC will show up in the app as it does on Windows.

When you connect to the Cloud PC, it open in full screen, which gives the impression that you’re running Windows 10 natively on the Mac. It’s a nice effect.

You can, of course, mouse to the top of the screen to display the Mac menu bar and the window controls for Remote Desktop. What’s missing is the File Explorer integration I saw in the Windows client, which lets you pass files between the remote and local computers. (This might be available optionally, I’m not all that familiar with Remote Desktop on Mac.)

From here, Windows operates normally. And for whatever it’s worth, the performance is terrific, at least for running a handful of bundled apps like Edge and Notepad. Perhaps yesterday’s performance issues were just a day one problem.

And as promised, everything was right where I left it. The applications and windows I previously had open were still open, and the taskbar customizations I made, such as pinning Notepad and Paint, were retained as expected.


To test Windows 365 on a Chromebook, I chose the HP Chromebook x360 14 that I sort-of reviewed recently. And I chose the web client, just to see what that was like, though I suppose the Android version of Microsoft Remote Desktop would work as well.

This was the simplest onboarding experience: I just browsed to the Windows 365 website in Chrome and signed into my Microsoft 365 commercial account. And then I opened my Cloud PC in the browser. The first screen I saw was interesting: I could optionally configure the Cloud PC to access my Chromebook’s clipboard, microphone, and printer, and enable a preview version of file transfer capabilities. I enabled all four.

After authenticating, my Cloud PC appeared in the browser tab and everything, as Microsoft likes to say, was right where I left it.

For a more seamless experience, I went full screen and unpinned the navigation bar, which otherwise takes up a lot of space. Nice.

Here again, the experience was mostly seamless, and there was a way in File Explorer to access the local file system. (In addition to the navigation bar’s “Upload new file” button, which also provides file interchange.)

It’s possible that the web experience is a bit slower than the native app, but it honestly felt pretty good.


Finally, I tried accessing Windows 365 on my iPad Air. As with the Mac, I downloaded and installed the native Microsoft Remote Desktop client, signed into Windows365.com in my browser and got a subscription URL, and then pasted that into Remote Desktop. However, I couldn’t get it to work: The app reported that “managed resources have not yet been downloaded,” and each time I tried the “Download now” link, I got a “Download failed” warning.

So much for that. So I tried the web client instead. As with the Chromebook, I was asked to access local resources, which I allowed, and the Cloud PC desktop appeared in a browser tab.

I only tested this briefly, and with touch support, not a keyboard and/or mouse. But it seemed responsive, even in windowed mode, and applications launched quickly. You can interchange files via that “Upload new file” button in the navigation bar, of course.

Even with this light level of testing, it’s pretty clear that Microsoft is delivering a mostly consistent Windows 365 experience across multiple devices and platforms. And for those organizations that need this kind of solution, that’s a good thing.

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Comments (17)

17 responses to “Hands-On with Windows 365 on Mac, Chromebook, and iPad”

  1. will

    I am curious if this could be a replacement for Parallels running on a Mac, once local resources show up?

  2. scottdetoffol

    I want a mix of a universal cloud-based profile with local machine applications and power. I want to login to my universal profile on any device and have access to my environment, applications, workflows and documents. Microsoft can manage the complexity of mixing cloud and local resources, taking advantage of whatever hardware I'm using at the moment.

  3. hallmanac

    Paul, there’s a setting in the MacOS RDP app that allows you to configure a local drive that can be used to pass files between the VM and the local machine. You need to go into the configuration of the remote PC and navigate to the “Folders” tab to set it up. Also, if you configure the connection to share your clipboard you can simply copy paste files between VM and local machine.

    I actually have the “MacOS-RDP-to-Windows-VM” setup as my daily driver. Been running it this way since January of this year. I'm a .NET developer who owns a MacBook Pro 16" (not the M1) and working remotely (i.e. from home). I purchased a Dell XPS 8940 desktop machine and maxed out the specs. I use that machine for gaming (as does my daughter) but I have Hyper-V running with a Windows VM that I use for my development machine. I'm connected to that VM from my MacBook pretty much all day. 

    Incidentally, I do have Parallels installed and did use it for about a year. I occasionally fire it up to keep things somewhat up to date just in case something happens to my other, but I have not had the need. 

    The reason I did this was two-fold. One, because I wanted a stable IP address from which I could connect to assets in Azure. Many of our assets are only accessible from whitelisted IP addresses. My home connection is a Gigabit connection (AT&T fiber) with a static IP address so bandwidth and rotating IP addresses is never an issue. I wanted to be able to work from other locations without having to whitelist a temporary IP address every time.

    The other reason I did this was to help with battery life on my MacBook. Running Parallels killed the battery in less than 2 hours which just annoyed me since this particular MacBook has a 100wh battery. Now that I use the Microsoft RDP app (same one that Paul showed above) I get the closer to 5 hours (I still have a lot happening on MacOS).

    I have to say, this has worked far better than I anticipated. My daughter has played Microsoft’s Flight Simulator at the same time I’m remoting into my VM debugging a large solution, running SQL Server, and a host of other demanding workloads. Neither one of us felt any impact of the other. That Dell XPS 8940 is a freaking dream.

  4. chrishilton1

    Do they not provide a boot to RDP install, which would make more sense. In the article it means you have to have an OS running first to boot into the 365 OS. I would want to use this on older hardware on which W11 will not run.

  5. danbear2929

    Trialing with this in my organisation which is fairly small and since most of my employees are out on the road for client based meeting having Windows 365 to access a cloud pc with all the internal sever applications and documents without registering their iPads into our organisation device management portal would be an awesome feeling.

  6. RobertJasiek

    Let me assume for the moment that I would accept a cloud at all, installation of Win32 32b and 64b softwares works, the initial problems on the iPad will soon be overcome, and full Windows Explorer file management and transfer is possible for an arbitrary number of files and folders per file action.

    Windows file management, software and operating system on an iPad is a most delightful thought. However, what does it cost?

    $20 per month is $240 per year or $1680 for my expected lifetime of an iPad. Prohibitively expensive! I would pay €140 once, which is the price for Windows 10 Pro on one computer. The price of the iPad plus €140 would be ok. However, the price of the iPad plus $1680 for Windows 365 Cloud is beyond words.

    • mprachar

      Anybody making that comparison is missing the point entirely. You are paying for a fully-functioning desktop environment in the cloud. The iPad is just one possible access method.

      The value of this particular all-in Cloud Windows Instance should be measured against other similar solutions...

      • RobertJasiek

        I understand your point and certainly there are uses for a fully functional computer in the cloud. However, my need differs: I just want Windows on an iPad. For that, I might build my own cloud server. What and how can I achieve this or is there no such option yet?

        • digiguy

          Yes you have a much more cost effective option, which I use everyday…. Remote desktop into a Windows PC with Jump Desktop, it will work just as well as Microsoft remote desktop, if not better (you have access to audio remotely too). No subscription, it’s just 15 or 20 bucks one-off…

          Even if you need to buy a dedicated PC it will be much cheaper than this solution of the long term and will be yours forever…

        • hrlngrv

          | my need differs

          Indeed. Not everyone needs a pickup truck or a circular saw. This isn't for you.

          OTOH, this is more evidence that centralized computing with local devices as thin clients may be the future.

        • bluvg

          You could build a VM in Azure, which is pretty much the same thing using a different cost model. But if you do go down this path, make sure not to put the machine directly on the internet: use a VPN or Remote Desktop Gateway or something in between. Azure has a VPN solution of course, and their AVD/W365 solutions take care of that isolation for you.

  7. bluvg

    I can see Chromebooks becoming a very popular "thin client." But Microsoft can still push people to Windows via licensing requirements and costs (previously VDA).

  8. anoldamigauser

    Will you be testing installation of a Win32 app on Windows 365?

  9. samp

    This might be a dumb question, but how about running it on an android phone? Would it work?

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