Migrating from Dropbox to iCloud Drive

I’ve been getting annoyed with Dropbox lately. First, this summer they redesigned the app to act as a “productivity launchpad” instead of a simple synced folder. I have nothing against this direction by itself, but this is not what I signed up for. Second, I’ve been paying both for Dropbox to store my files and iCloud to store my photos, so it felt a little redundant and wasteful. And last but not least, I had some privacy concerns as it’s yet another company having access to all my documents and files. The fewer companies and apps can reach them the better.

At the same time, Apple announced that iCloud Drive folder sharing is coming to iOS and macOS Catalina this spring. My Photos library took only a small part of 2 TB iCloud, and in general, I trust Apple’s privacy policies the most, so it felt like a good moment to give it a try. It took some time to migrate and find alternatives for specific use cases, so I wanted to outline some of the steps I took.

Connected apps

I started with going to Settings → Connected apps and reviewing who had access to my files. Some of the apps I didn’t even use anymore, but they could still read and write to either one specific folder or the whole Dropbox account. I revoked access from almost everyone as I was migrating away.

Moving design assets to GitHub with LFS

Our design team relies on a shared folder in Dropbox for accessing design assets for all our products. As iCloud Drive folder sharing is not available yet (and even when it will be who knows how stable it is in the beginning), I had to look for alternatives. Abstract made me think of using Git — this way we’ll get not only syncing but also a clear history of changes. By default, Git doesn’t work well with large files, but that’s been solved with Git LFS extension – inside Git it replaces large files with text pointers to an external server, so things are kept fast and tidy. GitHub supports it, so I created one repository per project with consistent names (product-design-assets) and shared README files that act as a table of contents for all assets. So far this approach has been working well for us.

Moving large files to Synology

While doing files inventory I realized that I have gigabytes of archives and videos that I keep only for reference and rarely use, so I moved all of them to Synology. It’s been my reliable local storage for the last 3 years and I just love this thing. (One day I want to write about how I use it for photography, as a media center and file server.)

Switching to Dropshare and S3 for screenshots

I’ve been relying on Dropbox’s built-in screenshot sharing tool and now needed to look for an alternative. In fact, I wasn’t really happy with it even before — in most cases, I’d prefer to share a simple image without any webpage wrappers, but there was no easy way to do it. I bought the Dropshare app and set it up to work with my Amazon S3. That thing is well designed, powerful, and customizable, so I wholeheartedly recommend it. (If you want to use standard macOS shortcuts with Dropshare, first disable them in System Preferences → Keyboard → Shortcuts → Screenshots. In spite of the help article saying it won’t work it does.)

Using Transmit for accessing Dropbox files

In addition to a personal Dropbox account, I also have another for work. I rarely need to access anything in it, but these moments still happen and I didn’t want to keep a Dropbox app installed and running just for these rare occasions. Luckily, I learned that Transmit can access Dropbox just like any other server. This way I can still work with Dropbox files without actually running Dropbox on my computer and giving it all the necessary (and abundant) permissions.

Disabling “Optimize Mac Storage”

With work files out of the way, I moved all my personal stuff to Documents folder in iCloud. I prefer to turn off “Optimize Mac Storage” in iCloud Drive preferences to make sure that all my files are always available to me. While this “optimization” was enabled I faced constant slowdowns and issues with apps like Alfred or Sublime Text which couldn’t access their preferences as they were in a cloud.

Bumps along the way

This migration wasn’t completely smooth. I had a scary moment after turning on iCloud Drive on a fresh Mac when files from a few weeks ago started appearing on my Desktop and in Documents. I have no explanation as to why this happened but it fixed itself after a few minutes — old files disappeared and correct ones showed up.

I also feel like it’s been less reliable on iOS than Dropbox — a couple of times I’ve been getting “The file can’t be opened” error when opening my files and only iPhone restart fixed it. iOS 13 wasn’t the most polished release in Apple’s history and they even had to postpone iCloud Drive folder sharing for half a year, so hopefully, they will get to polishing and fixing these issues soon.

Recently I’ve been reinstalling macOS Catalina from scratch on my laptop and for the first time in almost a decade Dropbox wasn’t the first app I installed on a fresh system. Actually, I didn’t install it at all. Between iCloud Drive, Git LFS, and Transmit I don't really need it anymore. Steve Jobs was right after all — “Dropbox is a feature, not a product”.