In a recent set of software updates, Apple has begun asking users if they would like to store the contents of their Desktop and Documents folders in iCloud Drive (Apple’s Dropbox-like repository for files and folders “in the cloud”).

I’m not a fan.

The idea here is to upload everything in these two folders to your iCloud account and keep it all in sync, across multiple computers. While this seems like it might be a good idea, the current implementation has some drawbacks and things to consider before simply checking the box:

1. If you have lots of files and folders (i.e. Gigabytes) on your Desktop or in your Documents folders, enabling this feature will require you to pay for extra storage space in your iCloud account. Uploading that much data over your internet connection could take days/weeks. This isn’t clear in the initial setup dialog.
2. Enabling this feature means you have to pay attention to whether a document is stored “locally” or “in the Cloud”. For files/folders which are only stored in iCloud, you must be connected to the internet to work with them.
3. Disabling the feature isn’t as simple as unchecking the box – there isn’t a simple ‘undo’ command which puts things back they way they were previously. This can be scary because unchecking the box makes everything disappear from your Desktop and Documents folders. The process of disabling the “Documents and Desktop in iCloud Drive” feature requires multiple manual steps to restore the files and folders to their original locations. Here are the instructions:

http://osxdaily.com/2017/07/06/disable-icloud-desktop-documents-mac/

I recommend against enabling this feature in the first place: