On Nov 28, 2009, at 9:42 AM, Ciprian Dorin, Craciun wrote:

   Maybe someone could clear this out (at least from GnuPG part). (My
original post was related with both GnuPG an OpenSSH).

~~~~~~~~~~ Original post:

   (I have a very basic question that to most of the persons reading
this news-group might seem trivial. But anyway...)

   My concern (as stated in the subject) is related to the security
strength of GnuPG and OpenSSH secret / private keys in the following
context:
   * the secret / private keys are encrypted by using a password that
only me (the owner) knows;
   * an attacker is in possession of my secret / private key files;
   * the attacker wants to gain access to the secret / private key
(thus being able to impersonate me);
   * the attacker chooses as attack method to brute-force the files
off-line, by trying to guess my password;
   * (by guessing the password I mean trying all possible passwords
that fit a given pattern; the password is not a dictionary word, but
instead is (truly) randomly created (i.e. DiceWare);)

   The question is: what does GnuPG or OpenSSH do to slow down
password brute-force? I mean does the password derivation function use
some iterations? If so how many? Can I configure them? I guess so but
I couldn't find any data on the net on a quick search. (Any references
are appreciated.)

GnuPG (really OpenPGP) does iterated password hashing. See section 3.7.13 "Iterated and Salted S2K" of RFC-4880 for the fine details, but the gist is as you surmised - the passphrase is run through many hash iterations. This slows down passphrase guessers as they must also repeat the hashing part the same number of times. By default, GnuPG uses 65536 iterations of the pasphrase hash, but can be configured via the --s2k-count option to be as high as 65011712 iterations.

Be careful though - in some cases, a too-large value can hurt you here. If you create a passphrase-encrypted message on a fast machine, and pick a huge s2k-count, and then try to decrypt on a slow machine (say, a cell phone), the message may become effectively unusable since the repeated hashes can take an unusable amount of time on the slow processor.

I'd have to look up the details if anyone is interested, but there was a case a few months back of a huge s2k-count actually causing an embedded device to trigger its deadman timer - someone had generated the message on a fast machine (so never noticed the large iteration count), but sent it to the slow one which clobbered it.

   Also, how many bits of security should my password have in order
to withstand an attack from a small / medium enterprise? (Government
is out of the question as they could get access to my infrastructure
by force...)

Difficult question to answer, since everyone is going to wave around their opinion. :)

I'd suggest starting with the various calculators on http://www.keylength.com/

David


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