How lawyers can securely use Dropbox with an iPad in 13 easy steps

The security concerns with Dropbox have been bugging me for a little while now, and I’ve let my brain ruminate. As you will recall, the problem with Dropbox is that (in theory, at least), it is possible for third parties to access data on Dropbox’s servers, perhaps without your permission. Dropbox might be served with a subpoena for all data on a particular server—which might include your client’s files. The risk is not great, but some lawyers are not willing to try to explain the low risk to their disciplinary authorities. (Like many lawyers, I’ve received a couple of those dreaded envelopes in my 20 years of practice. Nothing ever came of them (I only had to send in one response), but I know that pit-in-the-stomach feeling.)

Dropbox would be a simple solution if only it would encrypt data on its servers, like SpiderOak does. I wrote earlier about how to encrypt your data before uploading to Dropbox, and with one extra step we can use our iPads. Because lots of us use Dropbox, however, I figured it was time to design a sure-fire method that is as easy as turning your iPad on. I’m still trying to figure that one out, but for now there’s always this method:

1. Encrypt your data on your work PC. (I use the term PC generically here; it includes Macs.) Use TrueCrypt or any other encryption software to encrypt the files.

2. Upload your encrypted files to Dropbox. Drag the file container to your Dropbox folder, and a few minutes later it will be uploaded to Dropbox servers.

3. Go home (or wherever else you will access your files). This won’t work if you don’t have a PC at home, of course. At your home PC, make sure you have Dropbox installed and synced to the same account you use at work. Copy the file container from your Dropbox folder to your PC’s desktop.

4. Decrypt the file container on your PC. Of course, you’ll need to use the same encryption software that you have on your work computer—which is another reason I like TrueCrypt: it’s free and available for different platforms. No need to buy an extra copy of anything to run on your home computer, no need to worry about bringing a serial number home, etc. ONE THING: Make sure you’re decrypting the file on your desktop and not in your Dropbox folder!

5. Copy your files from your home PC to your iPad. This is the toughest part, perhaps. Using whatever method you have available to you, get the files onto your iPad. You can do it through iTunes (ugh) or using an app like Good Reader, make a wireless connection to your PC and copy the files over (probably the easiest way).

6. Work on your files on your iPad. Do whatever you need to do: read them, edit them, email them to someone. When you’re done, you’re going to reverse the steps above.

7. Copy the files from the iPad back to the PC. Easy to say, and hopefully you know how to do this already. I have to admit, even I can’t find a simple article on Apple’s web site that explains how to do this on a Windows PC.

8. Encrypt the “new files” on your PC. Gather up the edited or reviewed files that you just transferred to your PC, and use your encryption software to create the encrypted file container—just like you did at the office.

9. Copy the encrypted file container to your Dropbox folder. You may want to name your newer encrypted files so you’ll know which is which. As before, after a few minutes your new file container is uploaded to Dropbox’s servers.

10. Go to sleep/enjoy the rest of the weekend/etc. You probably don’t need instruction on this point.

11. At the office, copy the new encrypted file container to your PC. This will seem familiar by now.

12. Decrypt your files. Again, just like you did at home.

13. Copy the “new files” to the appropriate place on your computer or file server in the office. You probably do this dozens of times a day, so you don’t need me to explain how to do it.

That’s it: 13 “simple” steps. As I said, it’s a kludge, but it will have to do until a better option comes along. The problem with this method is that you have to have Dropbox and your encryption software installed on the computer where you want to access your files and get them to your iPad. If you’re counting on using a client’s computer, you will at least have to know how to install both pieces of software—and how to uninstall them when you’re done.

In case it wasn’t obvious, this article is written tongue-in-cheek. If you’re going to use your iPad to work on files at home or on vacation, just copy them to your iPad while you’re at the office—it’s as easy as that! (I suppose a situation might occur where you’d have to actually do all of this, like maybe your iPad cable was left at home and you can’t connect your iPad to your work PC.)


2 thoughts on “How lawyers can securely use Dropbox with an iPad in 13 easy steps

    1. Hi Dennis, thanks for your comment. This change might address my concerns, but I will have to dig into it a bit deeper. Stay tuned for an updated report…

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