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BoxCryptor: Sensitive Files on my Dropbox

One of the benefits from going paperless is having my documents at hand whenever and wherever I suddenly need them. That’s difficult for sensitive documents because storing these in the cloud is a no go. Since 1Password does not allow (yet?) to view and use files that are attached to secure notes within its iOS versions, I was looking for a different way to store these. Reader Malte pointed me to BoxCryptor which encrypts files on my Mac and/or iOS devices and (here’s the trick) integrates nicely with my Dropbox folder! I’ve installed and played with BoxCryptor now for a while and here are my first impressions. Just 4 words of warning: I already love it ;-)


First off – BoxCryptor is a typical freemium offer. And in my eyes the upgrade steps from the free version to the paid ones are set very reasonably. The free version is very functional already. I could buy options for multiple drives and for encrypting the file names for 29.99 EUR. The same extras sell for 69.99 EUR for business users. So for my purpose the basic/free version should do it – for now ;-)


Installation is easy. Within the typical Mac software install routine, I was asked to choose a folder where I wanted my encrypted files to live. I created this destination in my Dropbox. Then I needed to define a secure password which of course I stored as a 1password secure note.

BoxCryptor then created and mounted an extra drive on my Mac. This is the place where I’ll have to save the files that I want BoxCryptor to encrypt and automatically move to the secure folder in my Dropbox.


I created a text file and saved it to the BoxCryptor drive. The software did it’s job, encrypted the file and moved it to the folder that I had created during installation – on my dropbox.

Then I made a mistake :-) I tried to open the file in the Dropbox folder through the Finder while BoxCryptor was running and I expected that I’d be asked for the password. But to my surprise it opened the file just as any other file with even a preview being possible… So what’s the mistake? Did BoxCryptor fail? Did I miss to set a preference? Neither. A quick look at BoxCryptors support centre resolved it:

BoxCryptor Agent David Rajkay writes on Oct. 29th 2012:

…our main goal is providing security for the data not on your pc. The data you give away. If Boxcryptor is running everyone having physical acces to your computer can acces the files. If you want to add a layer of security you could add an application password. This password locks the BoxCryptor app. If you want to start it you will have to enter the password. If boxcyptor is not running no plaintext files remain on your Host.

This makes a lot of sense. And it offers some convenience for the workflows that I have in mind.

To finalise my test I tried to open the same file with BoxCryptor not running – and now it showed only the encrypted content – as advertised. Then from the Dropbox website – perfectly encrypted, too. Then checked to open the same file from within my iOS Dropbox App –  same thing. So far so good. Finally tried from the BoxCryptor iOS App – and sure enough was asked for my password as expected. After entering this, my text file showed – unencrypted. Perfect.


What does this mean for my workflows?

  1. Added security for sensitive files even on my Mac: The files on my mac are only readable if BoxCryptor is running. There’s a setting to not automatically start BoxCryptor at Mac startup. And of course I have set the password. So even on my Mac the sensitive data get’s an extra level of security. Good.
  2. Automated file operations possible: As the files don’t disappear in an extra application but are stored in my regular nested folders structure I can apply a lot of TextExpander naming standardisation and Hazel file management automation. And yes I can do this while BoxCryptor is not running as the software only manages the encryption process, not the file management.


BoxCryptor significantly upgrades my Dropbox. Dropbox excels at easy and reliable file syncing. I currently have 12 GB of free storage on my Dropbox account. More than enough for documents. But so far I could only use this for low or medium critical data. BoxCryptor extends the use scenarios for Dropbox significantly w/o interfering with Dropbox’s sync convenience. BoxCryptor is not a service but a fine piece of software that encrypts my data right on my computer. So if I use Dropbox for its sync magic, only secure files travel across the internet. Perfect teamplay.

The added security for sensitive files on my Mac and the fact that it allows TextExpander and Hazel to play out their standardisation and automation magic earn BoxCryptor a premium place in my system. Glad I was pointed to it! Stay tuned for updates on how it rates in my day-to-day use.

One Comment Post a comment
  1. Wonderful, exactly was I was looking for!

    I’m using iPhone/iPad with Windows and working on my own paperless workflow. I enjoy listening to Mac Power Users, but without Mac I have to find alternatives for Windows.

    I was researching how I could secure sensitive documents on multiple platforms. The best solution I had found was PDFTK Builder to encrypt PDF’s.

    With BoxCryptor I can now secure files inside dropbox and use PDFTK Builder to secure PDF’s inside Evernote. Although I still have to figure out how all this will fit into my workflow.

    2. December 2012

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