On Jan 9, 2014 7:16 PM, "David Tomaschik" <da...@systemoverlord.com> wrote:
>
> if the machine you are using for crypto operations is compromised, you have 
> lost (at least for the operations conducted while it is compromised)

Perhaps I'm wrong, but I don't entirely accept this. Surely if you are
signing with a key stored in an OpenPGP card being used via a
pinpad-protected reader, then - because the malware will not learn the
PIN - although the malware could potentially corrupt the message being
signed (or prevent it from being sent, etc), it could not do so in
such a way that a conscientious recipient already in possession of the
corresponding public key would mistake a tampered message for a
genuine signed message.

I would *guess* that there are additional operations that could be
performed, without disclosing secrets (e.g. PIN; raw private key), on
a compromised machine using a pinpad-protected reader. For instance,
generating new keys. (Although the existence and correctness of any
such generated keys would then have to be checked on a trusted machine
before being used in earnest, so there would not be much point in
using an untrusted machine for this task.)

> a smartcard without a PIN pad may compromise your pin (and allow arbitrary 
> operations while the smartcard is protected) but still protects the key 
> material itself.

Small comfort if the malware, knowing the PIN, can *use* that key
material every time the card is connected!

> Unless the malware has a history of all your previous email, an attacker 
> still doesn't have the key to compromise your past email.

I believe an attacker who knows the PIN and is able to execute
commands on the machine to which the card is connected (via
pinpad-less reader) has similar capability to an attacker who has the
private key file and its passphrase. His/her ability to decrypt any
messages in his/her possession is limited only by the bandwidth of
his/her connection to the relevant machine, the resources available on
that machine, and the alertness of that machine's legitimate
operator(s). Similarly re: signing and authentication.

> The smartcard (without a PIN pad) also allows for use of a lower-entropy 
> passphrase/PIN than Scenario 1 in the case of theft [...] (as the smartcard 
> locks itself after some number of wrong pins).

True. (Equally true, incidentally, of a smart card being used *with* a
pinpad-enabled reader.)

Even so, this is a pretty small advantage, given that it would take me
only a second or two longer to type a passphrase a couple of dozen
characters long than it would for me to type a PW1 half a dozen
characters long.

And given that a USB flash drive is much more versatile than an
OpenPGP card, and can be as compact as a SIM card-sized OpenPGP card
(i.e. *without the reader*) and less expensive in total, it's arguable
that the overall advantages of such a flash drive outweigh the
convenience of a low-entropy PW1.

> Theft of a key stored on disk is vulnerable to offline attack, theft of a key 
> on a smartcard is much harder to use (as the smartcard locks itself after 
> some number of wrong pins).  (This ignores three-letter-agency attacks 
> against the smartcard hardware to extract the key material from the EEPROM of 
> the smart card itself, bypassing the card applet.)

Allow me to "unignore" them :-) I assume that any agency likely to
have a chance of extracting a raw key from a sensibly passphrase
protected GPG key file, is likely to have a chance of successfully
extracting a raw key from a smart card's EEPROM; and vice versa. I'd
hazard a guess that the EEPROM attack is more feasible, but since I
can only speculate blindly on the matter, I prefer not to assume that
either technology has an advantage over the other in this particular
respect.

Best regards,

Sam

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