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The surprising takeaway for me is that PGP is so astoundingly crappy to use that even Phil Zimmerman asks people to send him plain text mail. We've got to do s

by acabal 13y ago

The surprising takeaway for me is that PGP is so astoundingly crappy to use that even Phil Zimmerman asks people to send him plain text mail. We've got to do something to improve the state of things here.

ChuckMcM 13y ago
Phil knew PGP was less usable than it could be because it was an add-on to SMTP. It was always hard to use. That said, I'm encouraged by some of the folks looking at building new systems for message store systems that are secure. They will need new clients of course but that seems to be reasonable.
- rdl 13y ago
  E-Mail has a moderately crappy experience on phones even without the security issues, so there's plenty of reason to build something new (with a new client) even if you're not worried about security. The thing that terrifies me about trusting Silent Circle for anything real is that if you're only on mobile, there is a huge amount of evil either of two US companies (or anyone who can put pressure on them) can do to you, and it's essentially a black box. Basically every security guarantee a mobile app makes can be subverted by Apple, Google, potentially some of their suppliers, and anyone who either puts legal or technical pressure on them. It can be done to individuals, rather than some pervasive backdoor which could be uncovered. To some extent, mobile carriers, who are essentially an arm of government in many places, could also attack users. Ubuntu Phone, Firefox mobile OS, etc. help in that they add more platforms, but don't seem to fundamentally improve security. The only thing which would really be viable, IMO, is a totally open hardware design and OS, where users get to pick their own update sources, and all the baseband crap essentially firewalled off into a little FCC-approved area which can't attack the rest of the device. And potentially with the entire baseband removable so you could have just a PDA, PDA+wifi/bt, or maybe in a future world, some novel radio protocols designed for protection from monitoring.
  - chakalakasp 13y ago
    This was my reaction as well to Silent Circle. If the attacker can own your OS, who cares how secure the app is? Silent Circle may keep things encrypted while going over the fiber and the wires and the airwaves, but what comfort is that when the government can remotely turn on your mic or camera?
    - rdl 13y ago
      There is probably a way to use Android safely, and hopefully a way to use iOS safely -- some kind of firewalled/VPN'd network, proxying any public traffic, and periodic checks for that. You'd ideally verify each OS version before doing updates, and maybe even do some destructive teardowns. I assume NSA plans to do something similar when DOD does smartphone deployments. There's potentially the SE Android stuff, too, but that's largely orthogonal to this. However, in the corporate BYOD world, or in the consumer world, it's probably not going to work.
david_shaw 13y ago
> The surprising takeaway for me is that PGP is so astoundingly crappy to use that even Phil Zimmerman asks people to send him plain text mail. I agree that that was surprising, but I can't take it without a grain of salt: he is the co-founder of a company releasing alternatives to e-mail+PGP for privacy. That's more than a small conflict of interest. I'm also not sure I understand his point regarding email privacy vs. message-app privacy. Either of them could easily be subpoenaed in the U.S., and moving either of those services off-shore should theoretically provide the same protection. Maybe the messages will be stored on Silent Circle servers in an encrypted state...?
- StavrosK 13y ago
  Silent Circle controls the client for Silent Text, so the messages can be encrypted end-to-end. For email, the same thing isn't true, so messages can be decrypted on the server (otherwise the mail client could never read them). Hence the discrepancy, and the deletion.
  - david_shaw 13y ago
    > For email, the same thing isn't true, so messages can be decrypted on the server (otherwise the mail client could never read them). I'm not a crypto guy, so forgive my potential ignorance. Are you saying that because the crypto is being done on a potentially untrusted client (whether a web interface or third-party email client), that the end-to-end encryption could be compromised? I realize that e-mail (by protocol) is sent over plaintext, but if the entire content of the e-mail is PGP encrypted, how is that less secure than actual end-to-end encryption?
    - JshWright 13y ago
      With email, you _can't_ encrypt the headers of message. Who the message is to, who it's from, when it was sent, what the subject line is... All those things need to be accessible to every server that touches the message from creation to delivery. Things get worse when you have to interoperate with mail clients that don't support encryption. Now the best you can do is encrypt the body of the message at rest, but you still have to be able to decrypt it to deliver it. You're absolutely right that _if_ both parties are using PGP in their clients, then the _body_ of the email will be secure, end to end (not the meta data mind you, just the body). However, that requires a lot of manual key management (assuming you use a client that supports it in the first place). That key management nightmare is why no one actually uses PGP...

by acabal 13y ago

ChuckMcM 13y ago

Phil knew PGP was less usable than it could be because it was an add-on to SMTP. It was always hard to use. That said, I'm encouraged by some of the folks looking at building new systems for message store systems that are secure. They will need new clients of course but that seems to be reasonable.

rdl 13y ago
E-Mail has a moderately crappy experience on phones even without the security issues, so there's plenty of reason to build something new (with a new client) even if you're not worried about security. The thing that terrifies me about trusting Silent Circle for anything real is that if you're only on mobile, there is a huge amount of evil either of two US companies (or anyone who can put pressure on them) can do to you, and it's essentially a black box. Basically every security guarantee a mobile app makes can be subverted by Apple, Google, potentially some of their suppliers, and anyone who either puts legal or technical pressure on them. It can be done to individuals, rather than some pervasive backdoor which could be uncovered. To some extent, mobile carriers, who are essentially an arm of government in many places, could also attack users. Ubuntu Phone, Firefox mobile OS, etc. help in that they add more platforms, but don't seem to fundamentally improve security. The only thing which would really be viable, IMO, is a totally open hardware design and OS, where users get to pick their own update sources, and all the baseband crap essentially firewalled off into a little FCC-approved area which can't attack the rest of the device. And potentially with the entire baseband removable so you could have just a PDA, PDA+wifi/bt, or maybe in a future world, some novel radio protocols designed for protection from monitoring.
- chakalakasp 13y ago
  This was my reaction as well to Silent Circle. If the attacker can own your OS, who cares how secure the app is? Silent Circle may keep things encrypted while going over the fiber and the wires and the airwaves, but what comfort is that when the government can remotely turn on your mic or camera?
  - rdl 13y ago
    There is probably a way to use Android safely, and hopefully a way to use iOS safely -- some kind of firewalled/VPN'd network, proxying any public traffic, and periodic checks for that. You'd ideally verify each OS version before doing updates, and maybe even do some destructive teardowns. I assume NSA plans to do something similar when DOD does smartphone deployments. There's potentially the SE Android stuff, too, but that's largely orthogonal to this. However, in the corporate BYOD world, or in the consumer world, it's probably not going to work.

david_shaw 13y ago

> The surprising takeaway for me is that PGP is so astoundingly crappy to use that even Phil Zimmerman asks people to send him plain text mail. I agree that that was surprising, but I can't take it without a grain of salt: he is the co-founder of a company releasing alternatives to e-mail+PGP for privacy. That's more than a small conflict of interest. I'm also not sure I understand his point regarding email privacy vs. message-app privacy. Either of them could easily be subpoenaed in the U.S., and moving either of those services off-shore should theoretically provide the same protection. Maybe the messages will be stored on Silent Circle servers in an encrypted state...?

StavrosK 13y ago
Silent Circle controls the client for Silent Text, so the messages can be encrypted end-to-end. For email, the same thing isn't true, so messages can be decrypted on the server (otherwise the mail client could never read them). Hence the discrepancy, and the deletion.
- david_shaw 13y ago
  > For email, the same thing isn't true, so messages can be decrypted on the server (otherwise the mail client could never read them). I'm not a crypto guy, so forgive my potential ignorance. Are you saying that because the crypto is being done on a potentially untrusted client (whether a web interface or third-party email client), that the end-to-end encryption could be compromised? I realize that e-mail (by protocol) is sent over plaintext, but if the entire content of the e-mail is PGP encrypted, how is that less secure than actual end-to-end encryption?
  - JshWright 13y ago
    With email, you _can't_ encrypt the headers of message. Who the message is to, who it's from, when it was sent, what the subject line is... All those things need to be accessible to every server that touches the message from creation to delivery. Things get worse when you have to interoperate with mail clients that don't support encryption. Now the best you can do is encrypt the body of the message at rest, but you still have to be able to decrypt it to deliver it. You're absolutely right that _if_ both parties are using PGP in their clients, then the _body_ of the email will be secure, end to end (not the meta data mind you, just the body). However, that requires a lot of manual key management (assuming you use a client that supports it in the first place). That key management nightmare is why no one actually uses PGP...