Dropbox did this before using a kernel extension, so that it can hook into the kernel kauth framework. The issue is that you need to intercept file I/O to make transparent sync work. But if dropbox is just another proprietary piece of software running hacks, I can’t really blame Apple. Or at the very least, they could have attempted to publish a standard. And it's much easier to understand and work with than manually managing selective sync. Why not? It's a very handy feature for a lot of users who don't have the disk space available to store their complete Dropbox folder. Perhaps shouldn’t exist in the first place That said, this hack (pretending your files are on disk) is arguably a fragile one, and perhaps shouldn’t exist in the first place (assuming it’s not a networked file system, which I believe it’s not). Dropbox cannot afford to simply throw their hands up and blame the users for not being technical enough. Non-techies will find it incredibly annoying to map individual subtrees leading to missing files, upfront sync costs when you need those, and running out of disk space. I don’t know how others do it, but I assume that you’d have to manually maintain mappings between a subtree in the cloud to one on disk, or alternatively run out of disk space if you want to have everything synced. This way it will not be deleted and replaced with the normal desktop folder upon restart and logging in.I agree, but I think it’s important to point out: I believe the main feature they need is to sync the full file tree without having to download the actual files until needed. EDIT: But there is a workaround: once the desktop folder is turned into a symlink that points to the desktop folder in the dropbox folder, go to the "Home" folder, and 'get info' on the Desktop alias/symlink and check the box "Locked" in order to lock the folder. Unfortunately, this by itself results in only partial success: on Catalina, so far as I've seen, after restarting the computer, the desktop reverts back to normal desktop configuration (no longer functioning as a symlink pointing into the corresponding desktop folder in the dropbox folder). per these instructions EDIT: this is also effectively what Alex Szatmary suggests). The natural workaround (the second way) is to (i) place the desktop folder contents in a folder within the Dropbox folder, then (ii) effectively turn the actual desktop folder (stored in the user folder) into a symlink (e.g. As the questioner notes, this method is no longer supported by Dropbox. This is how I used to have things until the latest dropbox updated (apparently triggered by my updated to Catalina) broke this method. The first way is to create a symlink within Dropbox that points to a folder outside Dropbox and will trigger Dropbox to sync its contents. So far as I know, there are only two possible ways to do this, and neither ways are available as of the latest macOS (Catalina, 10.15) and the latest dropbox updates (EDIT: it turns out that there is a workaround for the problem with the second way!).
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