How To Use Dropbox and TrueCrypt To Securely Transfer Files Privately

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by Bill Rounds: Anonymous
Web Surfing



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


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!

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.


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
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.

with permission from How to

6, 2011

Rounds, J.D. is a California attorney. He holds a degree in Accounting
from the University of Utah and a law degree from California
Western School of Law
. He practices civil litigation, domestic
and foreign business entity formation and transactions, criminal
defense and privacy law. He is a strong advocate of personal and
financial freedom and civil liberties. This is merely one article
of 73 by Bill
Rounds J.D.

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