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dropbox truecrypt

How To Use Dropbox And Truecrypt To Securely Transfer Files Privately

by Trace Mayer, J.D. on November 2, 2010

Reading time: 5 – 8 minutes

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 exteremely 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.

WHAT IS TRUECRYPT

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!

THE ECONOMICS OF ENCRYPTION

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.

HOW TO USE TRUECRYPT

WHAT IS DROPBOX

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 100GB for $9.99/month or $99.99/year, 200GB for $19.99/month or $199.99/year or 500GB for $49.99/month or $499.99/year.

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

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 archtectiure 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.

A HANDY TRAVEL TIP

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 embassay!

CONCLUSION

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.

Therefore, 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, convience and protection to be gained.

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25 comments

ABOUT THE AUTHOR: Trace Mayer, J.D., holds a degree in Accounting, a law degree from California Western School of Law and studies the Austrian school of economics. He works as an entrepreneur, investor, journalist, monetary scientist and operates Run To Gold. He is a strong advocate of the freedom of speech, a member of the Society of Professional Journalists and the San Diego County Bar Association. He has appeared on ABC, NBC, BNN, many radio shows and presented at many investment conferences throughout the world. This is merely one article of 41 by .
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{ 17 comments… read them below or add one }

1 Tammy Hawkins November 2, 2010 at 1:49 pm

Great article! I have recently started using Dropbox and LOVE how simple it is and that I can share my folders. In the past, if you wanted to share original image files with a family member or friend, you would have to email them 10 emails with a couple photos in each since they would be too large to send all together. Now I just load them all in and “share” the folder with whomever I want.

I’ll have to do a little more studying with the TrueCrypt. Hopefully that works simply too and isnt too complicated.

2 Trace Mayer, J.D. November 2, 2010 at 2:22 pm

They are both really simple. Do you use the Public folder function with Dropbox? Because if you share folders with someone it uses up space in all accounts. TrueCrypt’s user interface could be a little easier but once you get the hang of it it is really easy.

3 George November 3, 2010 at 10:01 am

Is there a way to setup TrueCrypt so that only the changed parts of files need to be uploaded? It seems like this would be really neat to use in conjunction with say, Wuala.

4 Trace Mayer, J.D. November 3, 2010 at 10:04 am

I do not think it would be a TrueCrypt issue but the various uploading/cloud software you use. I think that is how Dropbox works, it only uploads the parts of the file that change. This could pose a minor risk if someone is sniffing your traffic as it could give some indication about what could possibly could be in the volume but I think it is a de minimas risk and nothing to be concerned about.

5 A B November 11, 2010 at 10:16 pm

Great write-up, thanks!

Here is another software that can be used to protect the Dropbox folder:

http://www.winability.com/password-protect-encrypt-dropbox-folder/

6 Justen Robertson December 1, 2010 at 8:54 am

@George: I don’t know if a differencing system could handle encrypted files, it would depend on whether the system operated locally on the unencrypted source or remotely. If remotely, no, it will not work, because there’s no way to do a differencing comparison on encrypted files.

Truecrypt and Dropbox are both excellent pieces of software but this article could have beneffitted from a step-by-step tutorial. There are plenty out there, granted, but it would have been easy to do and got a lot more people involved.

As for breaking strong encryption of the type offered by truecrypt, it doesn’t just take a couple thousand dollars when you factor in the investment in equipment and payroll. Only a few companies and governments on the planet have the computational power to break that kind of encryption at all and of the ones that do, only the NSA would actually dedicate the resources to it. The others, mostly the big cloud services and other massive computing clusters, would lose vast amounts of money if they had to take all those machines offline and dedicate them solely to cracking your personal files. Not even the largest botnets have the practical ability to do it on the criminal side of things. The electricity bill alone probably amounts to a few grand over the week or two average it would take a large cluster to break twofish.

To get through multiple layers of encryption and obfuscation is too expensive to contemplate except when dealing with the most dangerous criminals on the planet. Unless your name is Osama bin Laden you’re probably good. That’s all assuming you use the tools right and observe security procedures of course. Most encryption breaking is low/no-tech. It’s a lot easier to dig through your trash for post-it notes with your passwords written on them or to plant a keylogger on your desktop (or even to film over your shoulder as you type your password on your laptop at the airport terminal – protip: get a biometric device like a fingerprint scanner for your mobile computing needs, don’t use passwords).

7 Steve April 4, 2011 at 3:29 am

Hi,

Truecrypt is a great program, but I prefer Axcrypt simply because it’s not only opensource – like Truecrypt – but because it’s easier to use.

Steve

8 UNF April 16, 2011 at 1:48 am

SpiderOak integrates both features (user-side securely encrypted + cloud storage) in one package, has 2GB free, automatic file de-duplication, previous version recovery, etc., and works across all platforms. I much prefer it to DropBox!

https://spideroak.com/

9 Saucer April 26, 2011 at 11:56 am

Its funny how everyone says that Truecrypt should be made easier. Its simple as it is lol. Then you got the other people promoting there products on this site like USBCrypt, which buy me now option pops up on the side. No thanks. Ill stick to Truecrypt, Tried trusted and true….also FREE and open source! ;-)

10 April December 13, 2011 at 8:30 am

Is there a way to mount a Truecrypt container on an iPad or iPhone? I have both Truecrypt & Dropbox working wonderfully. I also have Dropbox syncing to my iPhone & iPad. The only problem I have is that I cannot open the container on those mobile devices. Therefore any files I need to access on them, I have to leave unencrypted in Dropbox…defeating the purpose of Truecrypt.

11 Elwood Nose March 10, 2012 at 9:47 am

Thanks for the simple explanation of a key file! It never occurred to me that it could be ‘any old’ file. Obvious, but greatly enhances security.

12 David May 16, 2012 at 5:29 pm

I’m still wondering about that true crypt container being synced so many times in dropbox. It may be leaving traces of changes that will be easy to piece together over the course of several months.

The big elephant in the room these days with true crypt is the lack of BYOD (bring your own device) portability from smartphones and tablets. You simply cannot get your data on true crypt on a smartphone or tablet unless you use an app like logmein ignition or goto my pc. There is another product called securezip by pkware. This is a very robust encryption product used by many government agencies and companies. You can encrypt with digital ids and even view your encrypted files on your smartphone/tablet with their new securezip reader app. …still I wish securezip allowed key files also like true crypt.

13 Trace Mayer, J.D. May 16, 2012 at 6:01 pm

David, Those are great points.

14 Wally November 4, 2012 at 3:22 pm

Trace,

Just wanted to extend my sincere gratitude for the information you provide on this site, your commentary and the education this old man is embarking on with regards to Bitcoin, encryption and storage schemes/applications. You’ve given me a great start after seeing a YouTube video of you being interviewed recently. Best to you!

15 Trace Mayer, J.D. November 5, 2012 at 10:00 am

Wally, thanks. I am glad to help you take control of your privacy in an effort to defend your human rights.

16 pgoz March 10, 2014 at 6:14 pm

Dropbox in the appstore is now limited to ios 7. Do you know where I can still find an ios 6 compatible version?

17 pgoz March 14, 2014 at 1:59 pm

I found dropbox 1.4.6 on a file sharing website and sideloaded it with ifunbox. Now I am able to use dropbox on an older iphone that doesn’t have ios 7.

Trace: Could you clarify one thing about using them together? If I want to use dropbox to put files directly into my trucrypt container, then don’t I have to keep the trucrypt container mounted all the time? So somebody who steals my phone can see everything in the container, UNLESS i am able to unmount the container right away?

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