After years of being a paid Dropbox customer I’ve decided to replace Dropbox with iCloud Drive. Below I’ve documented the steps I followed to migrate. I’ve also included a few notes and links that may be helpful to others doing the same and for those who may be new to iCloud Drive.

  1. Enable iCloud Drive on Mac / iOS devices
    • Finder should now have an iCloud Drive link in the left sidebar
    • Files and folders stored here are synced to iCloud
    • Access this folder via CLI at the this path:
      • ~/Library/Mobile\ Documents/com~apple~CloudDocs/
    • For easy CLI access you will probably want to create a link in your home directory. You can create one named iCloud like this:
      • ln -s ~/Library/Mobile\ Documents/com~apple~CloudDocs/ ~/iCloud
    • iCloud Drive content can be accessed on other platforms:
  2. Ensure your Dropbox files are up to date and there are no uploads / downloads in progress
  3. Sign out of Dropbox on Mac
    • This stops Dropbox syncing on your Mac
    • Once signed out you will be able to safely relocate your Dropbox folder knowing that your content remains secure on Dropbox.com
  4. Move your Dropbox folder to iCloud Drive
  5. In iCloud Drive rename the Dropbox folder to something else (e.g. Docs)
  6. Wait for all the content to sync
    • The overall sync progress bar is in Finder next to the iCloud Drive icon in the left sidebar
      • Finder with iCloud Drive icon
    • The sync status of individual files and folders is displayed by showing one of a few possible iCloud icons next to their name:
      • Uploading icon cloud icon: uploading to iCloud
      • iCloud only icon cloud with a down arrow: file is in iCloud but not stored locally
      • Downloading icon progress bar: downloading from iCloud
      • ineligible icon cloud with slash: file is ineligible for syncing. It probably has a name that is ineligible or it exceeds the file size limit (currently 50GB)
      • A file without an icon is up to date
  7. Cancel Dropbox
    • Dropbox uses some dark patterns to make cancellation harder than it needs to be. As an example you will need to confirm cancellation on multiple pages and each time the cancel button gets a little harder to find. Be sure that you actually complete the cancellation process.
    • Your paid plan continues until the end of your billing cycle
    • When your billing cycle ends you will be downgraded to the free plan
    • When your plan is downgraded to the free plan your content may exceed the free quota limit. If this happens Dropbox will not delete your files but will prevent you from adding new files
  8. Restore original folder icons
    • If you previously shared a folder in Dropbox you will notice that Dropbox set a custom icon on the folder. It looks like the normal blue folder icon but has three people on it
    • You can find instructions on restoring original file and folder icons on this Apple support page
  9. TODO: Delete free Dropbox account
    • Will update when I do this
  10. TODO: Delete Dropbox apps
    • Will update when I do this