Windows 365 + the Microsoft RD Client app is how I’ve made my iPad into the machine I need it to be, complete with select Pencil support and a full OS that runs what I need when I need it.

This fits all the requirements I’ve wanted for so long:
- I can use my cellular iPad anywhere I have a connection
- I can use the Apple Pencil, a mouse, or a trackpad
- I can use my iPad tamed in a few ways to make it more useful to me
- I can use the iPad as an iPad for the 90% of things I like using an iPad for
- When I go on a trip, I know I can take my iPad and be fine. There’s no anxiety.
- It runs full, desktop-class Adobe Creative Suite apps
- I get the benefit of iPad-level battery life
Since we’re talking about an iPad, there are catches. And this does cost some money. Here’s the setup:
- An 13” iPad Pro, though any iPad would work. But screen real estate helps.
- A Windows 365 subscription at $66/month.
- The free Microsoft RDP (Remote Desktop Protocol) app.
- A mouse (my preference, but the Pencil, trackpad, or touch works)
Setting up Windows 365 for iPad
Microsoft took their “Windows everywhere” strategy and really ran with it. They offer a service called Windows 365, not to be confused with Microsoft 365 which used to be known as Office 365.
Windows 365 is a cloud PC. It’s a full Windows license that runs on Azure, accessible from any device, even a Mac or a phone. They have a zillion plans, including a free 30-day trial of a 2vCPU + 8 GB of RAM and 128 GB of storage option.
I ran the trial but quickly realized it wasn’t enough. The CPU oomph was passable, but I ran into trouble with the Adobe apps refusing to load or install because it perceived the RAM as 7.9 GB, not 8, and it requires at least 8.
So I bit the bullet and dove in on the 4 vCPU + 16 GB of RAM + 128 GB storage option for $66/mo. And, it works. It works pretty fine. Not amazing or great, but pretty fine.
- Windows 365 is technically touted as a “for business” feature. You can imagine how businesses might want these “thin client” or “cloud PC” options for staff out in the field or whatever. But nothing’s stopping any normal person from signing up.
- If you have a personal Microsoft account, as I did, that won’t work. You’ll have to create a new “Business” account, but it auto generates one for you with the @onmicrosoft.yourdomain.com suffix. And you can use this…forever, best I can tell.
- You can cancel billing anytime, with no fees.
- There are other, beefier options available but the price ratchets up. There are, however, a lot of pricing options to choose from.
- Once you go through the process of setting up an account and billing, it spins up a cloud PC. This takes about 10 minutes.
- When it’s done, you use the Microsoft RDP app on your iPad to create a new “Workspace”. In your Windows 365 Admin panel, it gives you a URL you just copy and paste in. Then you just give it your user ID and password and you’re in.
Voila, instant PC.
Neat features and limitations of Windows on iPad via RDP
Microsoft has done a genuinely great job of getting it’s RDP app to work wonderfully on an iPad.
- The Apple Pencil is supported, as a “pointer device”. To my surprise, Photoshop can even recognize the Pencil and its pressure sensitivity through RDP. I believe this all uses the built-in Windows Ink support common from the Surface line of hardware. It does not use or recognize the “squeeze” gestures or the Pencil Kit “menu”. It basically treats the Pencil as a Slim Pen, sans eraser end. And Windows only ever treated the Slim Pen as a defacto tiny mouse cursor.
- You can use a mouse or trackpad, but gestures aren’t recognized as well or at all. For instance, using my MX Master Mouse in Windows Cloud PC via RDP, even if I install LogiOptions+, does nothing. You get to mouse, left/right click, and scroll.
- RDP can use a built-in iPad screen keyboard, the Magic Keyboard, or any connected Bluetooth keyboard. It even intelligently switches between a Touch mode and a pointer mode if you have a mouse or trackpad connected.
- Windows has almost all of its native features. I’ve noticed it does not have a lot of options for screen resolution, but it will (after warning you not to) happily let you change the percent scale.
- I figured out that since it’s technically “for business” that Edge likes to default to a “Work” profile, but you can sign in with a personal profile and it works just as you’d expect. And you can install any browser or game from the web you want, like Chrome, Brave, Firefox, Arc, etc.
- Download speeds inside the Cloud PC are blistering fast. This is because it’s on a server, and a Speedtest.net report shows it running at 3000Mbps up and down.
- These Cloud PCs are clearly for business and will not game. Don’t even try. I couldn’t even get an old copy of Red Alert II to play. I think it’s something about the graphics in these things. The GPUs are non-existent, relying on CPU architectures just powerful enough to display pixels, so games think your PC has no graphics card. Because I don’t think they do.
- I installed Grammarly on Windows and it runs with all its native features, unlike on the iPad. Useful for drafting text on an iPad, then using Grammarly in Windows to do some heavier editing and revising before publishing with Google Docs, WordPress, Word, etc.
- Because Windows is running in the cloud, almost no processing is happening on the iPad beyond displaying the screen. This means you get all the benefits of the long battery life from the iPad. I could work 10 hours on this in Windows if I had to. You’d never get that with a Surface (my experience was about 5.5 hours).
- The screen is not crisp, but it is passable. It does not give me a headache or make me wary of using it.
- Using an Apple keyboard in Windows takes getting used to because Cmd, Opt, and Control are different than Control, Alt, and Function in Windows.
- You can copy text in an iPad app and paste it into Windows via RDP! It’s like a weird hybrid clipboard running across two operating systems at once.
- You can Cmd+Tab to switch out of Windows via RDP and back to your iPad apps, like iMessage. Assuming the app isn’t forced from memory, you can Cmd+Tab back into RDP and it’s right there with no hesitation, albeit with the Start menu opened because Windows thinks Cmd is the Windows Context key.
- You can just leave the Cloud PC running and even if your connection is disconnected, as it will do if inactive for a while, you can reconnect back and all your apps and windows are right there. It is your PC in the sky, for better or worse.
- If you install Edge on your iPad, you have a clever way of syncing some tabs and even files through its built-in Drop (akin to AirDrop) feature.
- I installed Dropbox on my Cloud PC so I can move files back and forth between the iPad and Windows. The offline storage and cloud sync is super handy here. Would also work with OneDrive or even iCloud Drive (though I’ve not tried either.).
- Windows 365 PCs are basically x86 architectures, so there’s no ARM-incompatibility problems here.
- After a week of solid use, I’ve had a couple of instances where I have to sign back in to my Windows Cloud PC because iPad OS kicked it from memory, which is kind of annoying, but it’s only happened a couple of times and I did bounce around between a bunch of iPad apps.
- 1Password installs on Windows in the Cloud PC, so all my logins sync. However, it won’t recognize a fingerprint scanner or Windows Hello or FaceID or TouchID. To the Cloud PC, it has none of those things (which is true), so I’ve noticed a quirk where in the browser 1Password wants to unlock but just displays a black screen where the Windows Hello/fingerprint scanner would be. Unlocking 1Password with a password via the app launched from the taskbar clears it.
- A lot of keyboard shortcuts and commands and swipes don’t work well if your keyboard lacks a Windows Key, but some do, like Ctrl+Shift+V for the clipboard history.
- You can install apps from the Microsoft Store just fine.
- Full MS office works, but requires you have a separate license. It’s not included as part of “Windows 365.”
Why not remote into a Mac instead of Windows?
I’ve looked at Macstadium and even have Jump Desktop running on my MacBook. Cloud Mac servers are expensive, and this already felt decadent enough. Jump Desktop relies on my MacBook being available, plugged in, and on a good internet upload speed. This is all fine and well for me, but even on my fiber internet with 3 Gbps upload pipe, it was sometimes choppy. Not a lot, but a little. Dragging windows around was always a little like moving a window stuck with bubblegum.
The Windows RDP setup is snappier. It’s faster, and frankly, it just feels smoother. I can forget I’m using a cloud PC with it. I don’t forget that with Jump Desktop or remoting to my Mac. I’m aware I’m always connected by a thin wire.
Also, Jump Desktop requires a ton of fiddling to get screen resolutions right. When you load a 14” or 16” MacBook Pro on an iPad screen, the display is severely letterboxed because the iPad and MacBook have wildly different display proportions. You can use an app like SwitchResX to create some custom profiles by forcing your Mac to display a resolution it’d never default to, but I never got it perfect to my liking and switching back and forth proved challenging for it. I frequently had to restart my Mac just to get it to “unhook” itself from a resolution that was more iPad like when I remoted in.
Windows has none of these problems. I’ve read that Apple supposedly makes their screen resolutions based on what they know their devices need. Windows, however, scales with vectors and math and just happily accepts nearly any proportion you throw at it. And it’ll force every other app to play along.
Why not just buy a Surface or other Windows PC?
I did that for a few weeks and did not like it. You see, Windows is fine, but the apps are mostly terrible. And the new ARM Surfaces (for now) don’t have a lot of apps I like to use, like InDesign, Apple Music, or a decent FTP client that doesn’t look like ass.
And a Surface, which gets me the pen input for Photoshop and Illustrator (when Illustrator ever comes to it), is expensive all-in at about $2,000. I could “lease” this Cloud PC for three years and still not have spent that much money. It’s just way cheaper.
Plus, the iPad is a genuinely better tablet. It is lighter, and the Pencil is better than the Slim Pen. I don’t think anyone disputes this, even among Surface fans. Surface fans will tell you a Surface is a “2-in-1”. It’s a class of its own. I still say the kickstand is great and I wish my iPad had that, too.
My solution has been to carry the iPad in a Slim Folio case (the kind that folds into a triangle, (I like this $25 ESR model that holds the Pencil in place in my bag), plus a desktop Magic Keyboard (the white one with a TouchID button that comes with an iMac, not the black foldy thing for $300), and a mouse. I prefer a mouse, but agree that the iPad works better with a trackpad.
All this to say: my iPad + MX Anywhere mouse + Pencil + white Magic Keyboard is lighter than a MacBook, has cellular, has more options for input, and I can treat the screen as modular, setting it up on a desk or lying it down to draw or write on it.
Further, the iPad is still there, running. I have Apple Music, Notes, Bear, Things, Safari (for testing webpages), iMessage, Day One, and all the perks of Apple’s ecosystem like all my Photos. And if I run into some silly problem, like the inability for a website to work on an iPad, I just tap into Windows, sign in, and do it there in Edge or another Windows browser.
The only similar setup is a Mac running Windows virtualized. Which is an option! But that lacks pen input and, for now, cellular options. (Tethering for a few hours kills my phone battery.) I can even play music from the iPad and control it from the keyboard or control center while in Windows. OR, I can run audio from within Windows, all connected to my AirPods. Neat! However, I tend to mute Windows so the notification jingle sounds don’t “cut” my iPad audio off. iPads can, alas, still only play one audio stream at a time.
Why not just use a Mac and an iPad like Apple intended?
I hear you, but I just don’t want to. I don’t think I’m alone in this. For one thing, I move around a lot. I bike a lot and walk with these things on my back. I don’t want to carry both because they’re expensive and that’s a bit of extra weight. I also don’t relish having lots of devices for environmental reasons.
And because I’m mobile a lot, my work is variable. Sometimes a person emails me and wants something and then, “Ugh, I have my iPad, but I need InDesign.” This happened just this week when a client asked at the last minute for some things to send to Staples to print for an event. They needed them within an hour or two. My files were from InDesign, and without a Mac, I’m sunk. Luckily, I had my Mac with me while I was out at lunch. But sometimes the iPad is better because I draw with it.
This meant every time I left the house I’d think, “Okay, I’ll take the iPad but if I need it for that 5% of things it can’t do, I’m stuck.” Windows as a Cloud PC removes all of that anxiety and keeps me in both ecosystems.
As I said, too, remoting to the Windows Cloud PC is more stable and visually more consistent than remoting into my Mac and much cheaper (about $30-$50 less a month) than a Mac server, too. In a week of solid testing, my Cloud PC has never been flummoxed, even when I was on cellular for hours yesterday. I had a good 5G connection; I’m under no illusion it’ll work the same in a bunker, but it freakin’ worked.
I’m not going to get rid of my Mac yet. For now it’s still better at super heavy file tasks in Photoshop or Illustrator, it can run heavy GPU tasks, and it can handle hardware input like microphones and screen recordings with a presenter camera better. All things I do from time to time. But those are things I can at least schedule around and know, “This is my Mac task.”
It’s a really good option using Windows 365. I recognize that $66/month or whatever you end up needing is “throwing money at the problem,” but all this requires money, and I don’t think it’s unfair to say Microsoft deserves to cover the costs of the data center, Windows, processors, etc. That stuff costs money. Maybe someday they’ll have a “personal” version that lets people sign up at different rates designed more for hobbyists and individual day-to-day users. But for now, it’s a good option at a price that is 1/3 the cost of a new Surface (which likely would not last 3 years anyway) without leaving the perks of Apple’s hardware and software.