Petraeus scandal - what would have been a better way to communicate electronically [closed]

Question

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

Answer 1

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.

Answer 2

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.

Answer 3

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.