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Giving iCloud Drive a try


Given recent discoveries about the Dropbox app hacking its way into the Finder on the Mac, and using a few gray-area tactics to get the permissions it needs, I started looking at an alternative. I tried iCloud Drive, and here are my findings.

Why iCloud Drive?

I chose iCloud Drive mostly to give it a chance. It’s a relatively new service, plus it integrates nicely with the Apple ecosystem. It has a few advantages relative to Dropbox: it has native Finder integration, which means it works seamlessly with the filesystem.

It works in a special directory (Documents), but it also works on the Desktop as well. That means that I could just work on my files the way I always do and everything was synced automatically.

A nice feature iCloud Drive has is Optimize Storage. With this option, the system automatically manages which files are stored in your disk and which ones stay in the cloud, whenever it senses disk space is low. So it gives priority to files you’ve opened recently, and it’s kind of hit and miss.

One advantage of this system is I can have more files in iCloud Drive than what fits on my local drive. With Dropbox you can, too, but it involves managing Selective Sync manually for your folders. So if you don’t sync a folder, you save space, but you can’t see it at all on you system. With iCloud Drive you see the full directory structure, and even query for file sizes, and it shows the real info of all files, even if they’re not downloaded locally. That’s a great advantage.

The problems

It’s kind of common knowledge that Apple is bad at web services. I feel bad repeating it, because I wanted to give it a chance, but the reality is, they’ve improved a lot, but still nowhere near the reliability of other companies.

For starters, the first time I started saving files to iCloud Drive, they wouldn’t sync to my iPhone. I searched lots and lots of support pages and forum questions until I found a convoluted process to fix it, which involved fully emptying the drive and deleting files multiple times (which were already filled with GB’s worth of files). It worked out at the end, and after that fix everything was syncing instantly as it should.

I say instantly, but the reality is Apple servers, for as modern and environmentally friendly as they are (100% running on renewable energy at the time), are still too slow for competing. They’re nowhere near what Dropbox or Google’s servers can handle in terms of reaction speed and upload speeds in general.

The third problem is a matter of interoperability. These last months I’ve been working on web development almost exclusively, so I’ve been using macOS the whole time. Lately I’ve started using Windows too for a while, and not having my files there has been a hindrance.

Curiously, iCloud Drive is supposed to work on Windows, but it didn’t for me. I enabled it, but I think it may fail because of the size of my online drive relative to the disk space available. But there’s no indication that that is the case. No low space warnings, no fail icon, nothing. It may be because there’s not enough development devoted to Windows at Apple (understandable), but it’s not like its a cryptic error that happens to one person in a million. It’s a core feature that just doesn’t work out of the box.

I’m sure there might be a fix or a workaround for that particular problem, but I’m just not willing to put the time to find it myself. It should be a given.


I’d say I’d like to give iCloud another chance in the future. The appeal is there, specially because of the Optimize Storage feature. But the lack of speed, polish and debugging, makes me not want to trust it with all my files. For that, I’m still leaning towards using Dropbox, even with its flaws. At least it’s consistent and fast. In terms of speed, interoperability and stability, I still find Dropbox to be the king of sync.

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