Replacing Dropbox With iCloud Drive

I’ve been using Dropbox for several years, and I can’t remember ever having a serious problem with it. It’s just where my files go. Lately, however, I’ve started wondering if it’s something I need to keep paying for or have installed on my Mac. The main reason is that I’m already paying for another cloud file syncing thing — iCloud Drive. It may not have all the features of Dropbox, but I feel as though my use of those features has gone down a lot in the last couple of years.

What’s Changed

There’s three things that would have kept me on Dropbox before recently:

  • Apps that rely on it.
  • Collaboration and sharing.
  • An uneasy feeling trusting iCloud Drive with all my documents.

At least two of these things have changed a lot. I’ll go through all of them.


I used to use text editors like Elements or nvALT on iOS and Mac for notes, but I’ve been using Apple’s Notes app for a while now, and it’s just fine. Other apps like Byword and 1Password include iCloud syncing as an option. I’ve been using iCloud for those apps for a long time now and I can’t remember the last time I had an issue. It seems like either everything I use has added iCloud as an option or I’ve moved to something else.

Collaboration and Sharing

Dropbox definitely has better sharing options. Where iCloud has these features, I have no complaints. I’ve used the collaboration feature in Notes and it worked great, but that’s about the extent of my use. Mostly I’m just not collaborating in this way as much as I used to. At work I’m using Trello or Google Docs, and in the rest of my life this just hasn’t really come up.

I’ll miss the ability to right click and generate a link for any of my documents, but Droplr seems like an okay replacement.

If I was still using shared folders as much as I was a couple years ago, I’d definitely be more tied to Dropbox, but I’m just not, so this has become a bit of a non-issue for me.

That Uneasy Feeling

I’ve had no problem syncing the things I have through iCloud in the last couple of years, but I just don’t trust it the way I do Dropbox to keep my stuff. I have no evidence or strong reason to think that — just a general feeling of unease.

Apple’s strategy has been to present everything as though nothing will ever go wrong with any of their software or services, and so the user doesn’t need a lot of tools to help recover when something does. Because it won’t. Ever.

All of Apple’s services just feel opaque. iCloud drive isn’t great as far as letting me know the status of my documents. If it did break in some horrible way, I have no trust that I would have a good way to get my stuff back.

Unfortunately I don’t see this changing.

My solution is to make sure I’m backed up and hope for the best. I don’t really know what else I can do to move forward other than to keep paying for multiple cloud syncing services forever. Hopefully it all works out.

Moving Forward

Currently iCloud is in the middle of uploading a couple hundred gigabytes of data that was previously stored in Dropbox. When that’s finished, I’ll move my Dropbox account to the free tier and uninstall the app from my Mac.

There’s going to be things that annoy me about iCloud Drive forever. I hate the way it gives each app that uses it a top level directory, and I really don’t like that it’s not just a folder in my home directory but instead has my files stuffed away somewhere non-obvious.

The strange feeling I have is that I’m not moving because iCloud Drive has gotten better than Dropbox, or even that it’s gotten as good. I’m moving because maybe it’s become sufficient for my needs. I’m purposefully not using what’s clearly the best thing on the market, because I think I’m willing to live without some of it’s features. Hopefully it’ll be good enough.