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Comment by vlovich123 | Hacker News Reader

I don’t believe it’s possible to estimate the amount of entropy in a password - it’s too short so then you have to evaluate it against a dictionary. That’s why things are moving to passkeys but NIST recommendations thankfully have finally been updated to stop recommending weird password rules.

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An important distinction that often gets lost is that entropy is a property of a probability distribution. A system to generate passwords has entropy, one specific password does not.

It's possible to read "hunter2" from /dev/random.

To infer entropy from a single password, the best you can do is to see if it falls within the domain of some known, low-entropy systems. This works ok in practice, but is very far from perfect.

Well, trying to infer entropy of a password by classifying it into the lowest possible low entropy system actually works well against brute forcing because brute forcing usually works exactly doing that.

That's the crucial point. You can have a super high entropy probability distribution straight from a quantum lava lamp, but if it gives you "hunter2" as a password, you should still not use that password, no matter the entropy of the distribution.

Right, I was just about to ask: Entropy is the measure of how "surprised" I'll get from the next character in the password. It's not a property of the password, it's a property of me. "Γεια" is very surprising to everyone here, as everyone would assume the first character to be English, but not if you know that the user is Greek.

To be fair, one specific password does tell you something about the entropy of the generator. If I can grab 1 MiB of data from your password generator, I can probably estimate quite well the entropy of the generator. 10-20 bytes? That tells you almost nothing (but still not nothing). That means there must be some way of updating an estimate of the entropy of the generator from every additional byte of output and the amount of confidence that you gain about that estimate grows (probably exponentially) with every new byte.

But your password is 10-20 bytes so you can say nothing about the generator.

>NIST recommendations thankfully have finally been updated

Finally? It's almost been a decade since since special publication 800-63B was published recommending against silly things like composition rules and arbitrary password rotations.

The NIST guidelines have changed "should not" to "shall not" for 800-63B this year. The reason this is important is that the very first NIST guidelines recommended rotations and composition rules. Even after 800-63B was first published, people continued to use the earlier guidelines under the assumption it was better and the "should" wording let them keep doing it. The shall change should force a broader change which is why it's significant. Another notable change this year is the banning of security questions:

> Verifiers and CSPs SHALL NOT impose other composition rules (e.g., requiring mixtures of different character types) for passwords and > Verifiers and CSPs SHALL NOT require users to change passwords periodically. However, verifiers SHALL force a change if there is evidence of compromise of the authenticator. > Verifiers and CSPs SHALL NOT impose other composition rules (e.g., requiring mixtures of different character types) for passwords.

> Verifiers and CSPs SHALL NOT prompt subscribers to use knowledge-based authentication (KBA) (e.g., “What was the name of your first pet?”) or security questions when choosing passwords.

Estimating entropy is challenging because it's a reverse process from how it ought to work. I created https://phrase.shop, which generates passphrases with a known quantity of entropy. Hover over any of the three action buttons to see exactly how many bits of entropy will be used to generate the passphrase.

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