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Since it hasn't been mentioned yet, OS X and iOS already support S/MIME encrypted email, and having the private keys live on users' devices and doing encryption

Since it hasn't been mentioned yet, OS X and iOS already support S/MIME encrypted email, and having the private keys live on users' devices and doing encryption of outgoing messages on users' devices is probably the safest setup.

bigiain 13y ago
Hmmm, I don't know if I'm being outrageously paranoid, but I'm resisting the temptation to put my PGP private key on my iPhone - because it'd be _way_ too easy for Apple to extract the key/passphrase if they were coerced by someone powerful enough, and those "powerful enough" have shown that they consider a court order granting them the private key used to secure 400,000 people's email is an appropriate tool when targeting a single individual. Once that's known, is it really such a stretch to assume that an already complicit PRISM partner might be convinced/coerced to monitor downloads of crypto-capablea app from their respective app-stores, and provide or allow backdoors to their OS that leak private keys? Maybe that's being overly paranoid, but in the "post Snowden" era, it might just be a sensible and pragmatic view…
- e12e 13y ago
  It's good to be paranoid - but if you don't trust Apple -- you'll have to be quite paranoid with your (and every other) iPhone you encounter. After all they might be recording all sound within range of the mic, for example. Or all text typed. Or both. AFAIK Apple is close to best in class when it comes to handling secure information (keys, pins etc) -- even if they're not perfect.
  - bigiain 13y ago
    My assumption is that if the NSA takes a specific interest in _me_ - then Apple and/or Google could be requested/coerced into making any iOS or Android device I was suspected of carrying do that. If I held a top security clearance in a country the US was interested in, or was a politician, diplomat, drug-dealer, or Occupy Movement organiser - I wouldn't be happy using a modern smart phone. As a "nobody", I doubt the NSA would burn those resources on monitoring me. On the other hand, I wouldn't be _too_ surprised to find the NSA take special interest in anybody who's downloaded a PGP/GPG app from the App Store or Google Play - and if I worked for the NSA I'd certainly have entertained the idea of working out how to subvert iOS/Android to expose private keys and passphrases using privileged vendor-provided OS access. And I doubt I'm anything like as smart/creative/evil as the best people working at the NSA… (And Apple definitely talk best-in-class talk about secure data handling, but there are some interesting questions about how your old passwords/iMessages/keys re-appear on a new iOS device when you replace them…)
- dingaling 13y ago
  > I'm resisting the temptation to put my PGP private key on my iPhone S/MIME doesn't use PGP keys, it uses X509 certificates. You can quite easily deploy multiple certificates, one for each communication partner or channel. So for example your mail sent to / from your iPhone would be encrypted with one cert, whereas from your desktop for Super Secret Stuff you'd use another.

bigiain 13y ago

Hmmm, I don't know if I'm being outrageously paranoid, but I'm resisting the temptation to put my PGP private key on my iPhone - because it'd be _way_ too easy for Apple to extract the key/passphrase if they were coerced by someone powerful enough, and those "powerful enough" have shown that they consider a court order granting them the private key used to secure 400,000 people's email is an appropriate tool when targeting a single individual. Once that's known, is it really such a stretch to assume that an already complicit PRISM partner might be convinced/coerced to monitor downloads of crypto-capablea app from their respective app-stores, and provide or allow backdoors to their OS that leak private keys? Maybe that's being overly paranoid, but in the "post Snowden" era, it might just be a sensible and pragmatic view…

e12e 13y ago
It's good to be paranoid - but if you don't trust Apple -- you'll have to be quite paranoid with your (and every other) iPhone you encounter. After all they might be recording all sound within range of the mic, for example. Or all text typed. Or both. AFAIK Apple is close to best in class when it comes to handling secure information (keys, pins etc) -- even if they're not perfect.
- bigiain 13y ago
  My assumption is that if the NSA takes a specific interest in _me_ - then Apple and/or Google could be requested/coerced into making any iOS or Android device I was suspected of carrying do that. If I held a top security clearance in a country the US was interested in, or was a politician, diplomat, drug-dealer, or Occupy Movement organiser - I wouldn't be happy using a modern smart phone. As a "nobody", I doubt the NSA would burn those resources on monitoring me. On the other hand, I wouldn't be _too_ surprised to find the NSA take special interest in anybody who's downloaded a PGP/GPG app from the App Store or Google Play - and if I worked for the NSA I'd certainly have entertained the idea of working out how to subvert iOS/Android to expose private keys and passphrases using privileged vendor-provided OS access. And I doubt I'm anything like as smart/creative/evil as the best people working at the NSA… (And Apple definitely talk best-in-class talk about secure data handling, but there are some interesting questions about how your old passwords/iMessages/keys re-appear on a new iOS device when you replace them…)
dingaling 13y ago
> I'm resisting the temptation to put my PGP private key on my iPhone S/MIME doesn't use PGP keys, it uses X509 certificates. You can quite easily deploy multiple certificates, one for each communication partner or channel. So for example your mail sent to / from your iPhone would be encrypted with one cert, whereas from your desktop for Super Secret Stuff you'd use another.