I'm a Dropbox user working in a Mac environment. I'm experimenting with two different ways to sync two computers via Dropbox and also get the benefits of multiple off-site backup. I need advice on which approach to standardize:

  1. Some specialized folders I place directly inside the Dropbox folder in the Finder. That requires the least muss and fuss if I set up a new computer to sync with Dropbox.

  2. However, for my Mac's Documents folder, I place a symlink inside a Dropbox folder, so the Documents folder remains in its "usual" place on all of my Macs. That way, I don't have to think hard about in which folder hierarchy to save my routine work.

I'm thinking I should probably shift to one strategy or another, so I don't get confused, and use a single approach uniformly for all uses including Documents and also the "big" sync jobs like iPhoto and iTunes.

Does any one have a take on the pros and cons of either approach: that is either (1) move all such big folders into Dropbox and adjust where the i-applications on both computers look for them locally, or (2) use symlinks in such cases always?

What do you recommend, and why?

  • Are you using just Mac OSX? Or throwing Linux or Windows into the mix as well? How large is your Documents folder usually? Are they on the same network the entire time? Jan 28, 2012 at 20:30

2 Answers 2


I have been running using Dropbox folders almost exclusively for the last two or three years, in a mixed environment with Linux and Windows machines. Since the beginning of Dropbox, so to say. All my documents are in there, and due to some referrals, I don't have to worry about storage problems.

Putting everything into the Dropbox


  • You get an easy synchronization and setting it up on another machine is effortless
  • Over the time, you'll get used to using your Dropbox instead of the typical home folders
  • The setup is very transparent, there's no way to screw it up. You know where everything is.


  • You won't put your everyday documents where OS X assumes them, but this only matters in rare cases where for example programs (by default) open ~/Documents instead of the previously selected folder, etc.
  • You might run into space problems if you really keep everything in there. And it's a privacy issue as well.

To summarize:

This approach will work very well if you really use multiple computers (and not only Macs) at the same time. It takes a bit to get used to, but you can even choose to hide your usual ~/Documents, ~/Music, etc. from the Finder, by opening Terminal.app and entering:

chflags hidden ~/Documents

To reverse that, just enter:

chflags nohidden ~/Documents

Using symlinks


  • You'll stick to the default folder layout OS X prepares for you


  • It takes time to set up and is not always transparent
  • Your approach can get screwed up by programs that modify exactly those pre-defined folders. This is the main reason I don't choose to follow it. For example, my ~/Documents contains the folders Adobe, Microsoft User Data, Native Instruments, RDC Connections and Roxio Converted Items. Adobe alone takes 147 MB. I never put them there myself.

To summarize:

This works very well if you have a Mac-only environment. However, if you don't want stuff to be automatically added to those folders, or other machines will be used, use the Dropbox-native approach instead.

  • I can't tell you how it would work out with iLife libraries though (or iTunes, etc.), I've never tried that.
    – slhck
    Jan 28, 2012 at 20:41
  • Good answer, slhck, and thanks for the supplementary comment. Let's see if anyone else addresses that issue before I "accept" yours. One other disadvantage of (2) that I've experienced is that if you don't set up the symlink correctly and re-enable Dropbox too soon, you can actually erase the folder you're trying to sync. I did that once, and only the existence of a Time Machine backup saved me.
    – user115745
    Jan 28, 2012 at 21:02
  • Yeah, that's what I meant. As soon as you go to the Terminal to set up things that were not meant to be used this way, you're in danger. Although I wouldn't trust Dropbox to keep all of my data safe either — I experienced that once. Some files were just missing one day. Could have been a synchronization issue. Time Machine is your friend. Please wait until you accept the answer – you don't have to immediately do this –, I'd love some constructive input from a few other fellow OS X users on the site.
    – slhck
    Jan 28, 2012 at 21:05
  • @slhck This looks like another disadvantage: apple.stackexchange.com/questions/275283/…
    – eivindml
    Mar 5, 2017 at 21:35

I've gone with an exclusively symlink system for syncing my DropBox and my home machine for a single reason:

I'm terribly lazy.

That's it. I've got the skill to set up an extensive set of symbolic links once, but generally speaking not enough time/attention/willingness to carefully shepherd my documents to make sure they end up in the DropBox folders. I've been using OS X long enough now that I somewhat rely on my machine to drop files in predictable places.

Setting up DropBox symlinks so they pick up the files that end up in those predictable places means I don't have to manage downloads, where I'm saving files, etc.

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