Which is better … Box.com or Dropbox?  That is a question I get asked quite often.  In this so called new world of “cloud computing”, (the cloud has actually been around since the dawn of the “inter webs”) being able to effectively share files with others has become so common place that if you don’t have it … people look at you funny. And … it has a dramatic influence on those two, diametrically opposed forces: Productivity and Security.

So the first thing we have to ask is; “What do you want to do with it, what problem(s) do you need to solve?  Is it simple file sharing with a couple of friends?  Do you need to get files to people which are too large to email?  Are you thinking of replacing your aging local file server with a cloud solution?  Is this solution going to be used by a team of 4 or 400?  What is it you need your cloud-based file server to do?


From a 30,000 foot view, one can look at Box.com as the heavy duty, security focused, Enterprise level file and collaboration tool.  It is built primarily as an additional or primary storage platform for business use.  Dropbox on the other hand, from that same 30,000 foot vantage point, is “Stupid Simple file sharing for the rest of us!”  While it does have security (which we will see below) its primary market focus is in ease of use first … the rest follows.  Dropbox have announced (January 2014) that they are focusing their recent influx of capital on moving from “Your Files Everywhere”, kind of amateur “Thumb drive in the Sky” to more of an enterprise-ready model.  For the purposes of this post, we will discuss what is currently in place.

File Sharing

Since both Box.com and Dropbox mainly mainly provide the ability to store and share files, it naturally deserves it’s own section.  They do file sharing in a similar way, and on a small scale they operate about the same way. You set a certain folder to sync with the online service on your computer (see Syncing below) and those files and folder get synced to servers at Box.com or Dropbox.com.  Alternatively, from any web browser, you can log onto either site and upload/download files and folders at will.  For the most part, it works pretty well.

For both, when it comes to some of the proprietary Mac file formats; .pages, .numbers, .key etc, it can be a bit tricky.  These file formats are called “packages”, in which a document may appear to be a single file, yet it is really a folder with a number of other folders and files within it appearing as one file … which is called a package.  The images below show the file and then the contents of that file.  Notice the two images below.  One shows the file as it appears in the finder, and the other shows the file and folders it contains.

winning proposals complete


winning proposals package contents300

When syncing with dropbox, it treats the package file as a folder, as shown above.  When you upload that same file via the web browser, both services create a compressed file (zipped) to keep all of the elements together

browser zipped

When syncing with Box . com, that same file just produces an error.  This can be problematic if you are counting on having access to that file on other devices and counting on being able to open the file, not have to unzip.

package file error



On All Devices

Other than the file issues shown above, Box and Dropbox do a very good job regarding portable devices. The mobile app accesses your account and will render almost any file and will allow you to open files in other apps.


Pros: Things we like


  • Super simple to use.  Grandma would have no problems setting it up, uploading, downloading and syncing
  • Syncing with computers works better than Box
  • Computer syncing works with all file types (especially Mac package files, .key, .pages, .numbers)
  • You can select by device, what you want to sync.


  • Super secure
  • HIPPA Compliant
  • More granular controls on permissions setting.
  • Allows different permissions to be set on nested folders (folders contained within folders), so you can have, for example, a top level folder called “Projects” and sub folders for each individual project.  With Box, you can give permission to people for just the one individual project folder.
  • Simultaneous collaboration on files
  • Collaborate with outside users (those without an account)
  • Since it is built for and focused toward business, there is little chance of the intermixing of business and personal files

Cons: Things we would like to change


  • Less of a focus on security with a couple of security-related major blunders in the past
  • Not HIPPA Compliant
  • Since many users have their own account, it’s easy to have personal data syncing with business data filling up hard drives, account limits and internet bandwidth (imagine the internet bandwidth it would take to sync a business with 20 users will all of their personal photos, videos and music.  Although you can select what to sync, it’s hard to manage from an IT standpoint.
  • Can not set and control permissions on nested folders.


  • Web interface is dated and a bit confusing
  • Lack of real built-in photo and video browsing
  • Syncing is more difficult to setup when not using the predetermined folder location.
  • Syncing controls are on the web interface, not in the syncing app.
  • Syncing is based on account, not device. This means that what you are syncing to your iMac with a 1TB drive is same as you are syncing for your macbook air with a 128GB Solid State drive.


Bottom Line

If you are a small company and are willing to work around the security limitations, DropBox is definitely easier to use and they are working towards a more enterprise level platform.  If your main concern is security, Box is the way to go currently.  And … there is the added benefit of a clear distinction between personal stuff (DropBox) and work stuff (Box).  Again it comes down to Productivity vs Security.