To be clear, I want to use gnupgp to do symmetric encryption using AES256. As I understand it, the 'gpg -symmetric ...' command converts a pass phrase into a key, a 32 byte key in the case of AES256. I /assume/ that this conversion is 'deterministic' since as far as I can tell, the 'gpg -symmetric ...' does not store the key it generates. Correct me if I'm wrong.

I am trying to decide how long a pass phrase to use. I have not decided how to generate the pass phrase. Assume that it is pseudo-randomly chosen from the an english language character set.

On 4/4/14, 10:10 AM, Robert J. Hansen wrote:
Interesting math. However, I believe the OP mentioned they're generating the password and storing so human readable, i.e. English, isn't an issue.
What would be the recommended length for completely random characters
generated, for example, by a password manager such as keepassx?

Your questions are not clear enough to be answered.

"What would the recommended length for completely random characters generated, for example, by a password manager such as keepassx? If one were using the password as the symmetric key in libgcrypt? Or perhaps even just using openssl tools?"

1. Well, which password managers? Just because a character is completely random tells me nothing about how much entropy is contained in each symbol. "TTHTHHTTH" is a completely random sequence (generated it just now by flipping a fair coin), but it only has one bit of entropy per symbol. "fBTvC" is a completely non-random sequence, but it has a lot more entropy per symbol. Without knowing how a random password is generated I can't answer this.

2. Recommended for what purpose? 256 bits of entropy is wild overkill for almost all purposes. 128 bits of entropy is generally speaking plenty.

3. Which toolkit? libgcrypt and openssl are two completely different toolkits that work in completely different ways, and an answer appropriate for one might not be appropriate for the other.

4. What is it you really want to know? You already know: AES depends on having a 32-bit key which can support up to 256 bits of entropy. You've been told two good metrics for estimating entropy in a passphrase: 1.5 bits per glyph of English text, 5 bits per glyph of base-64ed random data.



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