How To Use Dropbox and TrueCrypt To Securely Transfer Files Privately

Recently by Bill Rounds: Anonymous Web Surfing

      Using the cloud to store and share files can greatly increase privacy and simultaneously remove the need for backups, border-crossing issues and risk of theft if a device is lost or stolen. Two extremely powerful defensive privacy weapons in your arsenal should be TrueCrypt and Dropbox. Because both are free and easy to use I recommend everyone become familiar with and use these exceptional instruments to securely transfer files privately.


TrueCrypt is extraordinarily easy to use encryption software that is free and open-source. With the TrueCrypt encryption software you are able to create a file which then acts as a volume, similar to a folder. When creating a volume you select the size of the volume and either a password or both a password and a keyfile which are used for decryption.

With TrueCrypt the keyfile is an optional and extremely powerful tool. A keyfile is a file, such as a .jpg, .doc, .pdf, etc., that is required in addition to the password to perform the decryption. But beware that if you cannot locate the keyfile you cannot decrypt the volume.

When a volume is mounted and open then you can add files to it just like a regular folder. You can put any type of file in the volume so long as all the files in the volume do not exceed the size limit you select when creating the volume. These volumes can be extremely large and 1GB of space is not uncommon. But when using TrueCrypt with Dropbox I recommend smaller volume sizes because of the time required to perform the uploading and downloading of the files. You do not want to be waiting forever uploading any changes if you are on a slow Internet connection in Timbuktu!

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The economics of protection in the Information Age weigh heavily in favor of freedom and against violence or extortion. For example, TrueCrypt is free and it takes about 10 or 20 seconds to mount and close a volume which then protects your information against snoops, identity thieves or other nefarious individuals.

Sure, even strong encryption like 256-bit AES or Swordfish which meets Department of Defense standards and is used by TrueCrypt can be broken but it requires thousands of dollars worth of resources and lots of time. This creates an exponentially expensive curve for the extortioner in terms of both time and money as you can create 100 encrypted volumes in less than 10 minutes for every volume that contains actionable useful information and then if someone were to try and access that information without your consent it would cost hundreds of thousands of dollars. Thus, the cost benefit analysis begins to weigh heavily in favor of the individual using encryption. And the more people who use encryption to protect their information against criminals the more likely it is that criminals will look for easier targets.


Dropbox is a creative and extremely simple solution to sharing files via the cloud. I really like Dropbox because it just works. A Dropbox account is free to setup and comes with a 2GB limit. Additional space can be purchased at rates of 50GB for $9.99/month and 100GB for $19.99/month. Once Dropbox is installed on your computer, laptop, iPhone, iPad, etc. you simply open the Dropbox folder and put files in it. Dropbox works in the background to upload the files and then sync all the other devices. You can also share folders with other Dropbox users which is great for collaboration.

For example, suppose you are working on a spreadsheet for a business presentation. Instead of saving the spreadsheet to your Documents folder on your desktop computer you would create a Documents folder in your Dropbox folder and save it there. Then when you are done working on the desktop computer the file will be automatically uploaded and encrypted, although Dropbox has the decryption key, to the Dropbox server. Suppose you then fly to a business meeting and realize you forgot the spreadsheet on your laptop. No problem. Just install Dropbox on the laptop and the business presentation spreadsheet will be automatically synced to your laptop.


Using Dropbox and TrueCrypt should appear fairly self-evident by now. For example, you can travel with a laptop that contains no information across borders and when you arrive at your destination just install Dropbox and sync with your files from the cloud. Because Dropbox has control of the encryption key you can use TrueCrypt for an added layer of protection. That way if the Dropbox servers were compromised for whatever reason the your files would still be encrypted.

Another wonder aspect of setting up your information architecture to use TrueCrypt and Dropbox is that you no longer need to worry about backing up the files. This can save lots of time and headache.


Many of us often travel internationally. What would happen if all our possessions such as wallet, laptop, etc. were lost or stolen? One form of insurance is to (1) scan both sides of all the contents of your wallet, credit or debit cards, passport(s), driver’s license(s), etc., (2) place them in an encrypted TrueCrypt volume and (3) place that encrypted file in your Dropbox. Then should you ever need to access the electronic versions of those documents you can do so quickly and easily. This could save you a ton of headache at the embassy!


By using the cloud to store and share files among many machines you can secure your privacy, protect your information against criminals, snoops and other diabolical individuals, remove the need to backup and provide a great form of insurance. Because TrueCrypt and Dropbox are both free to use I highly recommend everyone at least try these out to get familiar with them. There is nothing to lose but a few minutes of time and extreme amounts of privacy, convenience and protection to be gained.

Reprinted with permission from How to Vanish.

January 6, 2011