Defending People

the tao of criminal-defense trial lawyering

¡SpiderOak, Sí. Dropbox, No!

It is almost unfath­omable to me that a lawyer would give up con­fi­den­tial client infor­ma­tion with­out a fight.

Yet Sam Glover at The Lawyerist sug­gests that this might be an option: “If you are the sort of per­son who would fight such a sub­poena, this would give you the option to do so.”

The con­text: Glover is talk­ing about using Spi­derOak for file sync instead of Dropbox.

Drop­box and Spi­derOak both pro­vide options for syn­chro­niz­ing data between com­put­ers and stor­ing it in the cloud. While Drop­box has access to your data, Spi­derOak has zero-knowledge encryp­tion: data are encrypted on your end, and Spi­derOak could not decrypt them even if ordered to.

What that means is that if the bad guys want to get your clients’ data from Drop­box, they can get a sub­poena or a court order and serve it on Drop­box; not only can you not fight it, but you might not know about it. If the bad guys want to get your clients’ data from Spi­derOak they have to go through you.

If some­one comes to me with a sub­poena for clients’ data, I will fight it. If I am ordered to com­ply, I will decide whether the prin­ci­ple is worth going to jail. But I hold myself to a high stan­dard, and some­times I for­get that oth­ers’ stan­dards are lower. Maybe it’s accept­able for non-criminal-defense lawyers to give up clients’ con­fi­den­tial infor­ma­tion with­out a fight. So let us not be too hard on Glover.

Let us limit the dis­cus­sion to criminal-defense lawyers.

For online data backup in a criminal-defense prac­tice, Drop­box is not an option

Back­ing up data off-site is indis­pens­able. Sync­ing data among mul­ti­ple com­put­ers (home desk­top, lap­top, office desk­top) is invalu­able. Shar­ing data with clients is use­ful. To do all of this I used to use Drop­box. Once I con­sid­ered the con­fi­den­tial­ity impli­ca­tions, how­ever, I real­ized that it was a mis­take. Now I will use Drop­box to share with clients stuff that the gov­ern­ment already has, and some­times for shar­ing large non-sensitive files, but never for any­thing that would be dam­ag­ing to the client’s case if the gov­ern­ment got it. If the gov­ern­ment is going to sub­poena my files, I want to be the gatekeeper.

Glover, quot­ing Eric Coop­er­stein, points out that “Drop­box is more secure than any­thing most lawyers have used to secure their files from the Bat­tle of Hast­ings until about 5 or 10 years ago.”

This is prob­a­bly true—breaking into an office is less of a tech­ni­cal chal­lenge to the gov­ern­ment than sub­poe­naing files from Drop­Box. But Drop­box cre­ates a dif­fer­ent sort of inse­cu­rity from scrolls stored in a chest. With Drop­box, copies of the scrolls are held by a third party, and the lawyer has no idea what that third party is doing with them. Aside from the fact that sneak-and-peak war­rants are harder to get than sub­poe­nas, at one point Drop­box was claim­ing the right to use cus­tomers’ data. They’ve backed off on that claim, but the mak­ing of it was enough moti­va­tion for me to switch to SpiderOak.

Fur­ther, if any­one but you has access to your encryp­tion key (the case with Drop­box) then any­one who hacks them might have access to the key as well. With Drop­box, you’ve given a third party a copy of all of your scrolls; that third party has a dupli­cate of the key to your chest, which he keeps in his pocket with a bunch of other people’s keys; and there are a thou­sand thieves actively try­ing to pick his pock­ets. If you can’t imag­ine a dozen things that might go wrong, you’re not try­ing very hard.

If you are not the sort of per­son who would fight a sub­poena for your client’s records, I hope that you aren’t defend­ing peo­ple. If you are, I hope that you’ll take seri­ously the risk that Drop­box presents.

When a sin­gle data breach could ruin many clients’ lives, “rea­son­able” security—the stan­dard pro­pounded by Coop­er­stein and Glover (and appar­ently approved by bar associations)—is not good enough. Only the extreme will do.

(P.S. if you keep client data on a lap­top, go now and encrypt the hard drive so that when your lap­top gets stolen you won’t have to worry much about your clients’ secrets.)

Share

About The Author

Mark Bennett got his letter of marque from the Supreme Court of Texas in May 1995. He is famous for having no sense of humor when it comes to totalitarianism.

Comments

10 Responses to “¡SpiderOak, Sí. Dropbox, No!”

  1. Franklin Bynum says:

    I never used Drop­box when I was in pri­vate prac­tice han­dling trial cases, for the rea­sons you describe here. But since becom­ing more an appel­late lawyer, I keep the appel­late records (pub­lic doc­u­ments) and my briefs (will be soon enough) in Drop­box and have very much enjoyed the convenience.

    Were I to need an cloud encryp­tion solu­tion for trial prac­tice in the future, I would prob­a­bly still just use Drop­box along with a strong PGP key for files that need to be encrypted. (This would require some kind of stag­ing area or script to pre­vent from an unen­crypted doc­u­ment being uploaded to Drop­box, but that’s easy.)

    Sure, that way I forgo phone and tablet access, but I don’t need to be access­ing those doc­u­ments on my phone any­way; my lap­top is always at hand.

    PGP would allow gen­er­a­tion of a key pair for each client—attorney retain­ing the pub­lic key, client retain­ing the pri­vate one—so that she would always be able to access her own encrypted doc­u­ments: every doc­u­ment could be encrypted using both the lawyer’s pub­lic key and the client’s pub­lic key.

  2. Sam Glover says:

    I don’t dis­agree with any par­tic­u­lar point, but I think Dropbox’s “trans­parency report” is rel­e­vant: https://www.dropbox.com/transparency

  3. Mark Lyon says:

    I’ve long used http://rsync.net/ for my online backup needs. They under­stand secu­rity of infor­ma­tion and aren’t try­ing to be any­thing other than a file repos­i­tory — one that encour­ages ME to be in con­trol of my data (and encryp­tion). They even pro­vide the tools to ensure my files are encrypted on my end, in a way that keeps rsync.net out of them, since I con­trol the keys.

    Par­tic­u­larly inter­est­ing and attrac­tive was their War­rant Canary. They rec­og­nize that there are some sub­poe­nas that they can­not dis­close to their clients. So, instead, they reg­u­larly pub­lish an updated and signed text file with a recent head­line. If it’s not reg­u­larly pub­lished, one can safely assume that a war­rant has been served. http://www.rsync.net/resources/notices/canary.txt

  4. If you like drop­box but want another layer of secu­rity, you could use box­cryp­tor which lets you cre­ate an encrypted drive within drop­box allow­ing you com­plete con­trol over data access within that drive..

  5. Ross says:

    Good point on the hard drive encryp­tion. That should also apply to flash dri­ves and other remov­able media. I would tend to think that an attor­ney who loses data that isn’t encrypted has vio­lated some por­tion of the respon­si­bil­ity to clients rules. If I were on a jury where a client sued an attor­ney in that sit­u­a­tion, I would have no prob­lem find­ing in favor of the client.

  6. I’ve had noth­ing but prob­lems with Spi­derOak. It kept man­gling my data, los­ing files, chang­ing files while I work on them, etc.

    Now I’m back to Drop­box but with Viivo (URL is com­pany name). Every­thing goes into the Viivo folder first, which encrypts it and puts it into the Dropbox.

    Note that I am not a crim­i­nal defense attor­ney and am more con­cerned about iden­tity theft, and finan­cial infor­ma­tion than I am about gov­ern­ment war­rants. YMMV.

  7. Are you aware of any actual cases in which the gov­ern­ment attempted to access a lawyer’s files through a sub­poena issued on the lawyer’s 3rd-party doc­u­ment stor­age facil­ity? If this is all just spec­u­la­tion, I think you should let peo­ple know that.

    • Mark Bennett says:

      I “should”?

      I am not aware of any such actual cases. If the gov­ern­ment sub­poe­naed records from Drop­box, there is no rea­son that I or any­one would be aware. That is part of the problem—it could hap­pen with­out the lawyer know­ing it.

      Ethics are not a mat­ter of “fight­ing the last war.” Nor are ethics what the law says. Your answer—“this is bet­ter than we’ve done in the past, and is what dis­ci­pli­nary author­i­ties are okay with” sug­gests a stunted sort of ethics.

  8. Are you aware of any cases that subpoena’d Drop Box file or any other sim­i­lar ser­vice, secret or not, with a fight or not? Thanks.

Leave a non-anonymous Reply