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Not a security professional here but .... having read through how it happened, it's clear sending these emails from the shared account by Paula Broadwell was the problem (if I understand correctly). But would there have been a way for Petreaus to protect himself?

I would think tornetwork but that's probably has a lot of backdoors for military. Maybe some proxy setup or private vpn? Would it be possible to use a secure txt message way via phones? Honestly, maybe something as hair-brained as vps account that you ssh into? Would ssh be secure from the US government from a technical pov? If you feel compelled to answer, leave politics out of it.

thx in advance

update #1

So the basic facts seem to be the following. I am assuming these facts are given so obviously don't send unencrypted email is a given. Is sending pgp encrypted email ok, though? Is there a better sol'n? Using something as a shared drop with the capability of sending out emails seems to be the big problem, but what would be a good alternative? Honestly, these were both very smart people (and interesting to see the social element as the downfall). Basic Facts (feel free to edit):

  1. Two people shared a gmail account
  2. They used the gmail account for sending messages by leaving in the draft folder so that no incoming messages into their regular email accounts nor traces of emails on public servers, sniffed from traffic (and probably a myriad of other things)
  3. Sounds as if one of them (Paula Broadwell) sent an email to third party (Jill Kelley) who brought to attention of the FBI. Due to nature of email, she raised it to FBI who investigated.
  4. FBI probably got search warrant on gmail account and based on the email(s) sent by Paula Broadwell and the content in the communication in the Drafts folder, it was apparent that David Patraeus
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This is a questions and answers site about security, not a forum to discuss current events. There may be a security question here, but it is incomprehensible if one hasn't been following the same news reports about the Petraeus scandal that you have. Please make your question comprehensible by the 95% of the planet who don't live in the US, as well as to the 99.999999% who will have forgotten all about it in a couple of years' time. –  Gilles Nov 17 '12 at 21:38
    
if you think it's a current events question, then I guess you don't understand. –  timpone Nov 19 '12 at 16:21
    
Closed as too localised, but I was also tempted by off topic and by not a real question. Read @gilles comment and the FAQ for guidance. –  Rory Alsop Nov 19 '12 at 17:44
    
odd this is argued as not a real question when this is considered a real question: security.stackexchange.com/questions/24048/… –  timpone Nov 19 '12 at 17:47
    
@timpone In your original question, the only definition of the context was “sending these emails from the shared account by Paula Broadwell” (hint: there is no antecedent for the word “these” in your post) and the only definition of the security requirements is “a way for Petreaus to protect himself”. This requires intimate knowledge of US current events. Your update is clear on the context (thanks to the list of “basic facts”) but it's still not clear what the security problem is or how the FBI suddenly got involved. –  Gilles Nov 19 '12 at 20:04
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closed as too localized by Gilles, Scott Pack, makerofthings7, Iszi, Rory Alsop Nov 19 '12 at 17:42

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3 Answers

Don't send unencrypted email with secret information that can get you in trouble.

Ask others not to send you secret information through unencrypted email, and if you receive act like you don't understand the information.

The problem isn't a particularly a technological one; its they used public email (e.g., gmail) to transmit information that could get him in trouble if it becomes public.

Now if Patreaus had an secret account that no one knew about, and only accessed it through tor (or something), never had his name associated with it (e.g., Broadwell was instructed not to use his name), never saved emails to his computer, never left credit card statements with the VPS (e.g., she charged the credit card statements), etc he could possibly get away with it.

But then again, the US govt may not be too happy with a general having secret unmonitored VPS accounts sending out information to unknown parties.

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thx, it seems like the real breakdown was using an email account for a shared communication path for saving messages in the drafts folder. Her use of it for sending emails from that account was the downfall. What they needed was something like that, that didn't have the way to send out. Dropbox might be suspicious due to being on a specific port. –  timpone Nov 17 '12 at 5:36
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Am I going to regret posting this? Well, I hear the bad guys have already figured this out, so we might as well let the good guys know as well:

  • Buy 2 throwaway cell phones with cash. (So there's no credit card number linking the phones to any person).
  • Only use those 2 throwaway cell phones to call or text each other. Use your normal cell phone for normal calls. Never use your normal cell phone to call either throwaway phone or vice versa. Don't even put the throwaway phone numbers in the "contacts" list on your normal phone, and vice versa.
  • Avoid mentioning each other's name on the phone -- perhaps use pet names -- so if the calls are wire-tapped and recorded, it's less obvious who you are talking to.
  • (possibly excessively paranoid): Turn off all your phones and put them in a metallic bag when not using them, so it's not possible for the cell phone company to track their locations and deduce that your normal cell phone and your throwaway cell phone are always together.
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thx - the bad guys have definitely watched The Wire so not any secrets going out. I'm tending to think this is the closest to an answer but would really like a computer based sol'n (hardware by itself would be incriminating). I'd say your last point is not excessively paranoid; I wouldn't be surprised if it weren't sufficient. –  timpone Nov 19 '12 at 16:32
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Email necessarily leaves a trail. This is not true for all electronic communications techniques. Furthermore, if appropriate encryption techniques are used, even if a trail exists, nothing can be inferred about its contents.

There are dozens of messaging protocols and configurations that are secure against both eavesdropping and after-the-fact perusal; and in fact this is one of the most frequently re-implemented security applications. You really can simply take your pick.

The problem isn't finding a technology to use, the problem is getting the associated parties to actually use the technology. As a rule, people are slow or unwilling to learn new software and new technology, and instead prefer to try to find ways to make do with what they know.

Unfortunately, if what you know is email -- and not even email secured with S/MIME or PGP; just plain old email -- then there's really nothing you can do to make your conversation secret. And so we have yet another scandal.

EDIT
@timpone My point is that the fact that he used standard unencrypted webmail tells us absolutely nothing about PGP or any other secure communication technique. The fact that he didn't use any sort of encryption (while standard government communication uses best-of-breed encryption) is a function not of the secrecy of the message, but of the person he was communicating with. If it was a matter of state communicated directly to the President, it would not have been sent using a draft email stored in a shared Gmail account. This is specifically because the President's office is expected to know how to use encryption. A biographer is not.

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Could you name or link to a few of these of secure setups? –  David Cary Nov 19 '12 at 16:22
    
right, I updated the question. They clearly knew that standard secure email wasn't secure. Agreed that some ssh based sol'n might do the trick for person-person communication but might be other issues esp if secured email is used in conjunction with non-standard. Perhaps, the fact that these two people (one of whom obviously had the highest security clearance) used this strategy tells us something about the security of pgp. –  timpone Nov 19 '12 at 17:05
    
@timpone updated –  tylerl Nov 19 '12 at 17:28
    
thx tylerl, to best of my knowledge, he didn't use standard unencrypted webmail; they used gmail effectively as shared storage. She did use unencrypted email from the SAME account thus leading to the messages in the drafts folder. Clearly, she wasn't a standard biographer based upon her background in terms of information security. I was speculating about pgp and NSA - to be honest but I do find it interesting. Granted, there was an affair involved. –  timpone Nov 19 '12 at 17:45
    
@timpone I was speculating about pgp and NSA: This is not your test case for this speculation. Your test case is secret communication within the NSA or in an official capacity. Alternately, if cracking PGP-encrypted communication holds the key to preventing some nationally-significant disaster, then that's a test case. For example, IIRC there was a case where the US government was not able to crack a Truecrypt-protected drive WRT foreign state-sponsored terrorism, so there's a datapoint. –  tylerl Nov 19 '12 at 18:13
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