Apple’s iCloud Drive feature has matured to the point that several months ago I stopped using Dropbox on my Mac, iPhone, and iPad without having to dramatically change any workflows. I still interact with Dropbox on the web once a week to produce the 9to5Mac Happy Hour podcast, but iCloud Drive could totally replace Dropbox for me with a few additional features…

My iCloud Drive usage surged over the last few months for two reasons.

First, I have a great experience with iCloud Photo Library syncing my photos and videos across my devices. Storing 16,655 images and 1,459 videos takes up 212.78GB of iCloud storage for me so I’m just over the 200GB for $2.99/month plan. The next plan available is 1TB for $9.99 which I gladly pay to continue the experience, and that leaves a lot of free iCloud storage for other purposes.

Enter macOS Sierra last fall. Apple enabled Documents and Desktop syncing through iCloud Drive between multiple Macs, iPhones, and iPads. I have the available iCloud storage to go all in, so I have been since macOS Sierra was released. I’m not doing the two Mac setup anymore, but I do enjoy having access to files from my Mac Desktop and Documents folders when using my iPhone and iPad.

But iCloud Drive still lacks a few important features that make Dropbox more capable.


First is cross-platform compatibility. Dropbox has clients on iOS, macOS, Android, Windows, and the web, but iCloud Drive sticks to iOS, Windows, and the web. Web access does mean you can find your files on other platforms, however, and I’m personally fine with iOS integration alone.

iCloud storage does integrate with built-in apps and services like Photos and iOS Backup that don’t work with Dropbox, but Dropbox does a better job on iOS at playing back media files by streaming before completely downloading. Apple could catch up here, but these differences are also minor for me.

It’s sharing large files with other people where I fall back to Dropbox still. It’s not a storage constraint. I pay for and have the capacity available. It’s just not as easy yet.

You can email someone a large attachment and rely on iCloud Drive for delivery, but Dropbox is more straightforward with how it handles sharing. Simply upload your file to your Dropbox storage, then share a URL with someone else. That person can download the file even if they don’t use Dropbox.

This is how Benjamin sends me his local audio recording for the Happy Hour podcast every week. His file goes to Dropbox, he sends me a URL, I download the file, then he eventually deletes it.


iCloud Drive is available on the web through, but there’s no concept of sharing files with a URL like there is with Dropbox.

Selfishly, I don’t install Dropbox on my Mac anymore at all. If I need to share a file with someone using a URL, I go to the web portal to upload the file and create the link.

But if I did keep Dropbox installed on my Mac, Benjamin and I could use a shared Dropbox folder where he could put his audio file from his Mac. I could access it when needed, then delete it for both of us when done. But I just don’t want Dropbox installed on my Mac anymore.

I also happen to be paying for serious iCloud storage anyway, so doing more with it and not Dropbox would be better. iCloud Drive could add shared folders and URL sharing (email just really isn’t the way I want to share) and totally replace Dropbox in my life. Fingers crossed for this feature in iOS 11 and macOS 10.13 later this year.