11 ms·

Trying to Keep Your E-Mails Secret When the C.I.A. Chief Couldn’t

52 points by 001sky 14y ago

mtgx 14y ago
I've heard even choosing "Go off the record" in Gtalk, doesn't really protect you, as Google still saves them. It may be something they are not willing to admit, though. But again, it's just something I've read. I would suggest using Jitsi, an open source alternative to Skype, that encrypts both chats and calls/videocalls, when talking to another Jitsi user. The best part is you can still use your Google Talk/Facebook chat/XMPP/other logins. But it encrypts the conversations happening between them. https://jitsi.org https://jitsi.org As for e-mail either one of these (Except Hushmail which I've also heard has been compromised): http://www.makeuseof.com/tag/3-secure-encrypted-email-providers-online/ http://www.makeuseof.com/tag/3-secure-encrypted-email-provid... Or just write e-mails in a text file, encrypt it locally, and then send it to someone. It will be hard to anonymize who's sending it, though, unless maybe you create some new e-mail accounts using Tor, and then always using them through Tor.
- spindritf 14y ago
  > I've heard even choosing "Go off the record" in Gtalk, doesn't really protect you Go off the record[1] in your client instead and enjoy all the important protections, which include: encryption, authentication, perfect forward secrecy and deniability of the kind that you can keep denying everything even when presented with a word for word printout of the conversation. Why even give Google a chance to fail you? Sure, it can still be known whom you're contacting and when but otherwise, you're covered. [1] http://www.cypherpunks.ca/otr/ http://www.cypherpunks.ca/otr/
  - cllns 14y ago
    "Go off the record" is misleading, it has nothing to do with OTR, as one might assume: [1] http://webapps.stackexchange.com/questions/16931/how-does-the-googletalk-client-do-off-the-record-messaging/16937#16937 http://webapps.stackexchange.com/questions/16931/how-does-th...
  - aw3c2 14y ago
    From what I have experienced OTR only works if both clients are online at the time of messaging. It does not seem to encrypt when the recepient is offline. Can someone confirm or deny and maybe explain?
- jcr 14y ago
  > It will be hard to anonymize who's sending it Actually, there are well known and well tested ways to do it. You would probably enjoy learning about remailers and nymservers. http://en.wikipedia.org/wiki/Anonymous_remailer http://en.wikipedia.org/wiki/Anonymous_remailer http://en.wikipedia.org/wiki/Pseudonymous_remailer http://en.wikipedia.org/wiki/Pseudonymous_remailer It's a lot of work, and it's easy to make security compromising mistakes, but it is a very interesting topic to learn.
roedog 14y ago
Keep in mind that the email account was a private, personal account. His CIA email account wasn't compromised. I'm guessing that they know pretty well how to keep their email safe.
deleted 14y ago
[deleted]
loeg 14y ago
This article misses a few points. I'm not going to cover all of them, but here's my pet issue: Yes, you can access existing Gmail accounts over Tor. But in my experience, it is damn hard to create them over the anonymizing network. Google wants a mobile phone number, which of course defeats the point. On the other hand, Hotmail had no such requirement last time I attempted this…
- spindritf 14y ago
  > Google wants a mobile phone number, which of course defeats the point. Can't you just pick up a pre-paid sim card in a corner shop? You get a "burner" phone as a bonus.
  - 1337biz 14y ago
    I guess the problem here is the "convenience" factor. Reaching an acceptable level of privacy seems to be taking more and more effort.
    - loeg 14y ago
      Yeah, inconvenient security isn't useful.
  - DanBC 14y ago
    That geo-locates you to a cell phone tower. There is probably a bunch more stuff that anonymity-keen (tin-foil-hatters) people will mention; CCTV from the corner shop when you buy the phone and the sim, whatever you use to buy the phone and sim etc etc.
guelo 14y ago
Using Tor Mail seems like it would be very anonymous. Though if they're sniffing your traffic the Tor signature makes you look suspicious.
drivebyacct2 14y ago
This is a weird headline. Part of the issue wasn't that he didn't know how to secure it, it's about doing it relatively in plain sight when as many people are watching as must be when you're the head of the CIA.
trop 14y ago
Question: What is the innate security risk of using airport wifi? From the article's conclusion: It takes just one mistake — forgetting to use Tor, leaving your encryption keys where someone can find them, connecting to an airport Wi-Fi just once — to ruin you.
- napoleond 14y ago
  Whenever you use a WLAN (or any network, really), you're more or less at the mercy of that network's administrator(s). In the context of the article, it would be easy for whoever is in charge of airport WiFi to connect your MAC address to the Gmail address you thought you were using anonymously.
  - blake8086 14y ago
    What if you use a VPN?
    - napoleond 14y ago
      I'm not a security guy, but I don't see what would stop a determined adversary with control of the LAN from performing a MITM attack. Obviously, a VPN is still more secure than no VPN.
      - Jach 14y ago
        Don't VPNs use public-key authentication like one can do with SSH? If they do, it's immune to MITM attacks.
        napoleond 14y ago
        So sub "using airport WiFi" with "using airport without a public-key encrypted VPN" or "using airport WiFi with a public key encrypted VPN, but from a new device were the key isn't listed yet". The point is, people make mistakes.
      - kansface 14y ago
pinaceae 14y ago
the main issue is that any conversation in the internet gets saved. nothing is forgotten, ever. it might be encrypted, but that only delays reading it. you want a safer way to communicate. use the telephone, non-voip. the content of your conversation is temporary, there is no record. if someone is not listening in to your conversation right now, no evidence in terms of content stays behind. if it would have been petraeus, all we would know that he had a lot of phone calls with his biographer....
- tsotha 14y ago
  >you want a safer way to communicate. use the telephone, non-voip. the content of your conversation is temporary, there is no record. You assume. There's no technical reason for this to be true, however. Telephone conversations are digitized and could easily be saved by the millions. I once worked at a military base where they saved every minute of every telephone conversation, and back then storage was a hell of a lot more expensive.
- 1337biz 14y ago
  I think it is save to assume, that if an intelligence service is putting the effort into intercepting your email communication, they are most likely willing to intercept your telephone communication as well. Voice recognition software has been around for ages, and mainstream consumer products (DragonSpeak, etc) have become surprisingly good. Sure, they could have used prepaid mobile phones or voice scramblers, but then again they also could have just accessed their secret email account(s) just from public access points.
shin_lao 14y ago
If you have an intelligence agency from the first world at your back, you're in a world of pain and there's not much you can do. However keeping your mail secrets from your girlfriend and/or your boss is relatively easy. Secure passwords, two factors authentication, ciphered communications to the servers, S/MIME...
ableal 14y ago
[Off-topic] On my copy of that page, I got an ad to NYT's own content magnificently titled "Spatchcocking your turkey". (It leads to http://www.nytimes.com/2012/11/18/magazine/the-2-d-thanksgiving.html http://www.nytimes.com/2012/11/18/magazine/the-2-d-thanksgiv... , not a bad cookery piece but alas, only headlined "The 2-D Thanksgiving".) P.S. On topic, it occurs to me that email was not needed. For the purpose of revising a draft, any web file access would suffice: Pastebin, Dropbox, Bitbucket, whatever. Even better, an encrypted service like Wuala or Silveroak.
acabal 14y ago
I've been thinking a lot about email security and encryption in the past year. Especially since everything you send on, for example, Gmail is stored on their servers forever, even if you "delete" it, and even if you're super-paranoid and use your own mail servers, you'll be mailing other Gmail accounts that record your activity anyway. 10 years from now the government could mine your past communications in ways never before imagined in the era of paper mail and paper shredders. Things you said a decade or even two earlier that were innocuous at the time could be brought as evidence against you. Because of the nature of easily-copiable bits, the only real way to be secure in communications is encryption with something like GPG. But public/private keys are a completely unfathomable idea to regular people. Hell, they're even confusing to techies. Even if the concepts are understood, implementing and using them is cumbersome and error-prone to say the least. That's why I think the most important thing to be working on, from a social-importance perspective, is a way to make GPG-style encryption friendly, usable, and easily-grokked. The problem of good-enough encryption has been mostly solved, I think--we just have to get people to use it!
- trekkin 14y ago
  Try AES.io, or SilentCircle, or HushMail. There are encrypted communication services available, the problem is that most Internet users don't think they need encryption, or do not trust it.
Sami_Lehtinen 14y ago
Excellent points, this is just why I run my own servers and actually emails which are private are sent as links, messages and data remain only on my server and are deleted after 30 days. So even if someone still got that message with link, they don't have my message anymore. Btw. You can count how many of your friends are security experts and how many aren't, I'm pretty sure that ratio is quite bad. Anyway, for some uses your own tor hidden service is fine, it's quite easy to run if you're familiar with Tor and services. You can also use something better and more secure for communication than HTTPS and Tor, like SSH and BBS like interface. It reduces risk that people accessing your service with systems which aren't properly prepared to be secure won't store anything at all on disk. (Yes, it still could be possible to swap or hibernate some data if users are real failures.) Yet another option which I like is RetroShare, it's secure and keeps data private, but it doesn't inheritly hide connections between nodes, for that part you'll need another anonymization layer. For simplicity, I prefer to use self hosted message system with SSL and notifications can be sent with link or without link to users when required based on message content / subject / privacy level required etc. If users do have registered account, then they also might need to give their login credentials if required. My server also provides TOTP authentication as 2FA solution, for a few geeks who use it, including my self.

52 points by 001sky 14y ago

mtgx 14y ago

I've heard even choosing "Go off the record" in Gtalk, doesn't really protect you, as Google still saves them. It may be something they are not willing to admit, though. But again, it's just something I've read. I would suggest using Jitsi, an open source alternative to Skype, that encrypts both chats and calls/videocalls, when talking to another Jitsi user. The best part is you can still use your Google Talk/Facebook chat/XMPP/other logins. But it encrypts the conversations happening between them. https://jitsi.org https://jitsi.org As for e-mail either one of these (Except Hushmail which I've also heard has been compromised): http://www.makeuseof.com/tag/3-secure-encrypted-email-providers-online/ http://www.makeuseof.com/tag/3-secure-encrypted-email-provid... Or just write e-mails in a text file, encrypt it locally, and then send it to someone. It will be hard to anonymize who's sending it, though, unless maybe you create some new e-mail accounts using Tor, and then always using them through Tor.

spindritf 14y ago
> I've heard even choosing "Go off the record" in Gtalk, doesn't really protect you Go off the record[1] in your client instead and enjoy all the important protections, which include: encryption, authentication, perfect forward secrecy and deniability of the kind that you can keep denying everything even when presented with a word for word printout of the conversation. Why even give Google a chance to fail you? Sure, it can still be known whom you're contacting and when but otherwise, you're covered. [1] http://www.cypherpunks.ca/otr/ http://www.cypherpunks.ca/otr/
- cllns 14y ago
  "Go off the record" is misleading, it has nothing to do with OTR, as one might assume: [1] http://webapps.stackexchange.com/questions/16931/how-does-the-googletalk-client-do-off-the-record-messaging/16937#16937 http://webapps.stackexchange.com/questions/16931/how-does-th...
- aw3c2 14y ago
  From what I have experienced OTR only works if both clients are online at the time of messaging. It does not seem to encrypt when the recepient is offline. Can someone confirm or deny and maybe explain?
jcr 14y ago
> It will be hard to anonymize who's sending it Actually, there are well known and well tested ways to do it. You would probably enjoy learning about remailers and nymservers. http://en.wikipedia.org/wiki/Anonymous_remailer http://en.wikipedia.org/wiki/Anonymous_remailer http://en.wikipedia.org/wiki/Pseudonymous_remailer http://en.wikipedia.org/wiki/Pseudonymous_remailer It's a lot of work, and it's easy to make security compromising mistakes, but it is a very interesting topic to learn.

roedog 14y ago

Keep in mind that the email account was a private, personal account. His CIA email account wasn't compromised. I'm guessing that they know pretty well how to keep their email safe.

deleted 14y ago

[deleted]

loeg 14y ago

This article misses a few points. I'm not going to cover all of them, but here's my pet issue: Yes, you can access existing Gmail accounts over Tor. But in my experience, it is damn hard to create them over the anonymizing network. Google wants a mobile phone number, which of course defeats the point. On the other hand, Hotmail had no such requirement last time I attempted this…

spindritf 14y ago
> Google wants a mobile phone number, which of course defeats the point. Can't you just pick up a pre-paid sim card in a corner shop? You get a "burner" phone as a bonus.
- 1337biz 14y ago
  I guess the problem here is the "convenience" factor. Reaching an acceptable level of privacy seems to be taking more and more effort.
  - loeg 14y ago
    Yeah, inconvenient security isn't useful.
- DanBC 14y ago
  That geo-locates you to a cell phone tower. There is probably a bunch more stuff that anonymity-keen (tin-foil-hatters) people will mention; CCTV from the corner shop when you buy the phone and the sim, whatever you use to buy the phone and sim etc etc.

guelo 14y ago

Using Tor Mail seems like it would be very anonymous. Though if they're sniffing your traffic the Tor signature makes you look suspicious.

drivebyacct2 14y ago

This is a weird headline. Part of the issue wasn't that he didn't know how to secure it, it's about doing it relatively in plain sight when as many people are watching as must be when you're the head of the CIA.

trop 14y ago

Question: What is the innate security risk of using airport wifi? From the article's conclusion: It takes just one mistake — forgetting to use Tor, leaving your encryption keys where someone can find them, connecting to an airport Wi-Fi just once — to ruin you.

napoleond 14y ago
Whenever you use a WLAN (or any network, really), you're more or less at the mercy of that network's administrator(s). In the context of the article, it would be easy for whoever is in charge of airport WiFi to connect your MAC address to the Gmail address you thought you were using anonymously.
- blake8086 14y ago
  What if you use a VPN?
  - napoleond 14y ago
    I'm not a security guy, but I don't see what would stop a determined adversary with control of the LAN from performing a MITM attack. Obviously, a VPN is still more secure than no VPN.
    - Jach 14y ago
      Don't VPNs use public-key authentication like one can do with SSH? If they do, it's immune to MITM attacks.
      - napoleond 14y ago
        So sub "using airport WiFi" with "using airport without a public-key encrypted VPN" or "using airport WiFi with a public key encrypted VPN, but from a new device were the key isn't listed yet". The point is, people make mistakes.
    - kansface 14y ago

pinaceae 14y ago

the main issue is that any conversation in the internet gets saved. nothing is forgotten, ever. it might be encrypted, but that only delays reading it. you want a safer way to communicate. use the telephone, non-voip. the content of your conversation is temporary, there is no record. if someone is not listening in to your conversation right now, no evidence in terms of content stays behind. if it would have been petraeus, all we would know that he had a lot of phone calls with his biographer....

tsotha 14y ago
>you want a safer way to communicate. use the telephone, non-voip. the content of your conversation is temporary, there is no record. You assume. There's no technical reason for this to be true, however. Telephone conversations are digitized and could easily be saved by the millions. I once worked at a military base where they saved every minute of every telephone conversation, and back then storage was a hell of a lot more expensive.
1337biz 14y ago
I think it is save to assume, that if an intelligence service is putting the effort into intercepting your email communication, they are most likely willing to intercept your telephone communication as well. Voice recognition software has been around for ages, and mainstream consumer products (DragonSpeak, etc) have become surprisingly good. Sure, they could have used prepaid mobile phones or voice scramblers, but then again they also could have just accessed their secret email account(s) just from public access points.

shin_lao 14y ago

If you have an intelligence agency from the first world at your back, you're in a world of pain and there's not much you can do. However keeping your mail secrets from your girlfriend and/or your boss is relatively easy. Secure passwords, two factors authentication, ciphered communications to the servers, S/MIME...

ableal 14y ago

[Off-topic] On my copy of that page, I got an ad to NYT's own content magnificently titled "Spatchcocking your turkey". (It leads to http://www.nytimes.com/2012/11/18/magazine/the-2-d-thanksgiving.html http://www.nytimes.com/2012/11/18/magazine/the-2-d-thanksgiv... , not a bad cookery piece but alas, only headlined "The 2-D Thanksgiving".) P.S. On topic, it occurs to me that email was not needed. For the purpose of revising a draft, any web file access would suffice: Pastebin, Dropbox, Bitbucket, whatever. Even better, an encrypted service like Wuala or Silveroak.

acabal 14y ago

I've been thinking a lot about email security and encryption in the past year. Especially since everything you send on, for example, Gmail is stored on their servers forever, even if you "delete" it, and even if you're super-paranoid and use your own mail servers, you'll be mailing other Gmail accounts that record your activity anyway. 10 years from now the government could mine your past communications in ways never before imagined in the era of paper mail and paper shredders. Things you said a decade or even two earlier that were innocuous at the time could be brought as evidence against you. Because of the nature of easily-copiable bits, the only real way to be secure in communications is encryption with something like GPG. But public/private keys are a completely unfathomable idea to regular people. Hell, they're even confusing to techies. Even if the concepts are understood, implementing and using them is cumbersome and error-prone to say the least. That's why I think the most important thing to be working on, from a social-importance perspective, is a way to make GPG-style encryption friendly, usable, and easily-grokked. The problem of good-enough encryption has been mostly solved, I think--we just have to get people to use it!

trekkin 14y ago
Try AES.io, or SilentCircle, or HushMail. There are encrypted communication services available, the problem is that most Internet users don't think they need encryption, or do not trust it.

Sami_Lehtinen 14y ago

Excellent points, this is just why I run my own servers and actually emails which are private are sent as links, messages and data remain only on my server and are deleted after 30 days. So even if someone still got that message with link, they don't have my message anymore. Btw. You can count how many of your friends are security experts and how many aren't, I'm pretty sure that ratio is quite bad. Anyway, for some uses your own tor hidden service is fine, it's quite easy to run if you're familiar with Tor and services. You can also use something better and more secure for communication than HTTPS and Tor, like SSH and BBS like interface. It reduces risk that people accessing your service with systems which aren't properly prepared to be secure won't store anything at all on disk. (Yes, it still could be possible to swap or hibernate some data if users are real failures.) Yet another option which I like is RetroShare, it's secure and keeps data private, but it doesn't inheritly hide connections between nodes, for that part you'll need another anonymization layer. For simplicity, I prefer to use self hosted message system with SSL and notifications can be sent with link or without link to users when required based on message content / subject / privacy level required etc. If users do have registered account, then they also might need to give their login credentials if required. My server also provides TOTP authentication as 2FA solution, for a few geeks who use it, including my self.