Microsoft and Apple have long felt like the Montagues and the Capulets, but lately, it feels like that feud is gradually mellowing into a cordial, mutual understanding — without needing two young lovers to die to make it happen. We’ve seen earnest overtures in recent years rather than shots across the bow, bringing the platforms closer together without impacting their sovereignty; Microsoft has offered olive branches such as Phone Link for iPhone, while Apple makes begrudging concessions like the upgraded Apple Music app and the iCloud Passwords Windows app. It’s progress, but it’s still not enough — notably if you’re an iPhone user with a primary Windows computer.
Full disclosure, I switched from Windows to Mac, but I still have to keep a Windows PC around in the form of a gaming handheld. It serves as a backup PC, and occasionally I do use it to check emails, watch YouTube videos, and the works. As such, I’ve had to figure out how to get my iPhone cooperating with Windows so I’m prepared in case my Mac, I dunno, bursts into flames (you never know). Having an iPhone and a Mac will always be the superior combination, but if that’s not possible, here’s how to make your iPhone and Windows more like Romeo and Juliet — assuming they had a happier ending.
I use Phone Link (for calls, texts, and notifications)
With Android, Phone Link on Windows is deeply comprehensive. I’ve used it before with an Android device, and I have to give it to Microsoft for just how much it allowed me to do from my computer without touching my phone. Full access to texts and calls, focus modes, interactive notifications, audio playback, app access, photo access — and limited control of your computer from your Android phone, too. Surprising absolutely no one, there’s only a fraction of that functionality with a Windows/iPhone combination. To be fair though, this is kind of Apple’s fault for the limitations it imposes.
The process is easy. Just download the app on your iPhone and open it on Windows, follow the prompts, give the necessary permissions, and you’re in. Limited though it may be, it gets the job done for the basics. Being able to see notifications on my Windows PC, check my iPhone’s battery, and occasionally respond to messages and calls — without touching my phone — allows me to forget, however briefly, that on a Mac the experience would be far better integrated and smoother.
The elephant in the room is Microsoft’s atrocious history with privacy. I have to use Phone Link knowing that I have no idea how much of my data is leaving my device for Microsoft servers, what’s happening to it, or if Phone Link presents some security vulnerability just waiting to be exploited. Perhaps someday the open source community can produce a capable, privacy-respecting alternative, but so far the alternatives I’ve seen are not good enough for my needs. For now, though, I’m content with integrated notifications. The Apple ecosystem advantages I can mostly live without.
I use Blip and LocalSend (for file transfers)
AirDrop has ceased to be a selling point for the Apple ecosystem. Now, Android’s Nearby Share works with iPhones, and Android’s even copying the same AirDrop-style tap-to-send feature. Phone Link has a file sharing feature, but for me personally, there are much better options. When I need to send files over the local network, i.e., when I’m at home, I use LocalSend. Though it may lack the same integration as AirDrop and Android Quick Share, it is feature-complete, open-source, easy to use, and secure; it’s so good that when I need to send a large file from my iPhone to my Mac (or vice versa), I still prefer it over AirDrop.
A nifty, free alternative is Blip. I’ve lauded Blip in the past as a free app you should install as soon as you upgrade to Windows 11, and I keep it on all of my devices. Blip is great any time you don’t have a local network to fling files over or have a faraway recipient. Even though my Windows handheld and iPhone are virtually always on the same network, I prefer Blip’s sleek interface and how it allows one-step drag-and-drop file transfers between your registered devices. Really, the only complaint I have about it is my knee-jerk, privacy-enthusiast reaction to the fact that Blip does not use end-to-end encryption.
This is the app I’d also recommend if you’re the one friend with an iPhone and all your other friends have Android smartphones and Windows PCs. File transfers will be so easy that any blue-bubble/green-bubble rivalries will be forgotten. Arguably, both LocalSend and Blip are better than the integrated, proprietary file transfer options since for me they basically never have hiccups or connection issues like AirDrop et al. They just work.
I use Vivaldi, Joplin, and Readest (for browsing, note-taking, and reading)
If there’s anything I’ve learned about the Windows/iPhone life, it’s that having rock-solid, reliable cross-platform apps does the most to minimize headaches and ensure you won’t ever find yourself in a pickle when your data is confined to one particular ecosystem. Sadly, this means giving up a few of the ecosystem benefits, of which there are many in Apple’s ecosystem. But for a cross-platform arrangement, it’s worth that little sacrifice. For my browser, I use Vivaldi, a browser you should switch to. I wouldn’t have made this recommendation a couple of years ago, but the team at Vivaldi has been cooking, and a steady stream of updates has brought it almost on par with Safari — which says a lot, since Apple has fought bitterly to restrict iOS browsers to WebKit.
Apple Notes is amazing … until you want to access it on Windows. The finicky iCloud web interface is not my favorite. My recommendation, then, is to replace it with Joplin. I kid you not when I say I’ve tried every note-taking app out there, and this was so amazing that I could let Apple Notes go. The app requires you to use third-party cloud syncing to sync the notes (aside from its paid Joplin Cloud service), but that’s not an issue for a reason I’ll get to later.
Another hard loss on the app front would be Apple Books, the best reader interface I’ve ever seen on a non-e-reader screen to date. Readest eases the blow. It’s the closest thing in terms of reading interface customization, cross-platform progress syncing, and that minimalist, Apple Books-esque interface that I adore. I can’t buy books on Readest, but I wasn’t buying them on Apple Books anyway, instead favoring DRM-free digital bookstores.
I use OneDrive and BitWarden (for cloud storage and passwords)
Credit where credit is due, Apple does have a functional iCloud app that incorporates Apple Passwords. But I’m confident — based only on intuition — that Apple intentionally makes the iCloud app not great to push you to buy a MacBook. Why? Because the iCloud Windows app seems almost hand-crafted to infuriate. The UI feels thrown together, pasted onto Windows with only minimal file integration; file syncing is slow and opaque; it often gives me account errors for no apparent reason that I cannot resolve. On one occasion, all the files in my iCloud Drive reverted to versions of themselves from a couple of weeks earlier, an issue I deduced was caused by the Windows app. So, understandably, the 4.8 star average it has on the Microsoft Store is baffling.
I’ve turned to third-party cloud storage to keep my sanity. OneDrive is my top recommendation. I’ve never been in the habit of giving Microsoft compliments, but I have to hand it to the company for how well-integrated, reliable, and affordable OneDrive is. It certainly takes some cues from iCloud, sitting in the background and unobtrusively keeping all your files up to date. Importantly, it has an iPhone version that works great for backing up the important stuff, like photos. Also note that Joplin (the notes app) works fine with OneDrive, as well as other cloud storage solutions like Dropbox. I should also note that OneDrive works great on Mac.
Apple Passwords on Windows is surprisingly okay, but still not great and is bundled into iCloud rather than being a separate app. Instead, I recommend Bitwarden. It’s free, open source, feature-rich, and cross-platform. The app looks and works as great on iPhone as it does on Windows.
I don’t use Apple’s Windows apps. Here’s why
I wish to be objective where possible, and I have to admit that Apple’s Windows app versions are a far cry from how bad they used to be. Just a few years ago most of them were a reviled mess. Now, as I’ve said, you’ve got iCloud with a 4.8-star average, Apple Music with a 4.5-star average, and Apple TV with a 4.3-star average. But I don’t use any Apple apps on Windows — aside from iCloud for Calendar and Contacts access — for one simple reason: They all feel like afterthoughts.
Every one of these apps on the iPhone/MacBook is polished, beautiful, works smoothly, and is relatively bug-free. The same cannot be said for my experience on Windows. It’s not just iCloud; I get constant account errors when using the Apple Music app, and the Apple TV app struggles to run shows and movies at their native resolution. Then you’ve got apps that I would never even touch, like Apple Devices and iTunes, because neither surpasses the 3.0-star average. All of these apps feel like they exist just so Apple can say they exist and fulfill its obligation to Windows users. But I get the distinct impression that once these apps meet the bare minimum for functionality — i.e., they are not a raging dumpster fire — Apple forgets about them, perhaps again intentionally so since you might throw up your hands and get a MacBook.
Fortunately, some Apple apps have a third-party front end so I get access to Apple services without being punished by Apple’s seeming indifference. My favorite example is Cider, an Apple Music player that looks gorgeous and runs better — anecdotally speaking — than the native one. Largely, though, I recommend avoiding Apple services.
