A few tweets have started making the rounds about how companies must be doing password security wrong because they seemingly do magic. Let’s start with the simple one, password history. Here’s some musings on how I think some magic could be implemented without a huge loss of security.

This is pretty straight forward to solve. Keep a history of the hashes. When the user enters a new password, take the password they just entered, and see if it matches any of the password hashes in the history.

A password hash typically consists of a digest and a salt. I’d strongly recommend that each password in the history have their own salt, so don’t reuse salts when a user types in a new password. So a password history table might look like this:

salt digest version
salt1 digest1 1
salt2 digest2 1
salt3 digest3 2

And the user enters a new password because they want to change it. The check process would look something like this:

hash_alg_1(salt1 + newPassword) == digest1
hash_alg_1(salt2 + newPassword) == digest2
hash_alg_2(salt3 + newPassword) == digest3

If any of those are “yes”, then they’ve used a password in their history.

In real life, you are probably using something like bcrypt. Many bcrypt libraries put the salt, digest, and “version” (work factor) in to a single output separated by dollar signs. They also provide convenience APIs to make the verify process simpler. You give it a previous bcrypt output and a plaintext password, and it knows how to use the salt and the work factor to see if the hashes match.

This approach typically works pretty well. I’d also caution how long you would want to keep password history. Too long might mean keeping around hashes that are weak. Let’s say you were using bcrypt(8) a few years ago, but moved to bcrypt(10). Keeping that bcrypt(8) password indefinitely means you’re storing passwords with less-than-ideal strength. If the password history is ever stolen and the history is weak, then you might be giving the attacker clues as to a password the user is using on another site, or their password habits.

If you ever need to drastically change the password hashing scheme because it’s broken (straight, unsalted MD5 for example) I’d purge the history altogether. It’s too much of a liability to have lying around.

The trickier one is fuzzy password history, but it can be done in some limited ways. The trouble with hashes is, they either match, or they don’t. There is no good way today to see if two password hashes are related to each other.

You can however tweak the input of the plaintext when checking history.

Let’s say the user’s old password is “I<3BillMurray11” and they change it to “I<3BillMurray12”. A site might say this password is too similiar to a previous password. You might quickly come to the conclusion they are storing passwords in plain text, or reversable encryption.

The site also could simply try a few heuristics on the input. It’s well known that when a password needs to change, users might cop-out and just increment a number at the end. So when the user types in a new password, check the history. No matches? Well, does it end with a number? Yes? decrement it and try the history again.

You are certainly limited to how much fiddling you can do like this. Good password hashing schemes like bcrypt are by-design not fast (to counteract offline brute force attacks). So checking hundreds of things is quite slow.

You can however use this to try a few of the worse offenders. Incremented trailing numbers is a very common one, same with addign a letter. Try chopping off a letter from the password end and see if it matches the history. Password history for a user should also reasonably fit in to memory, so doing these checks in parallel is doable, too.

Those are just some examples, and things that I think security engineers can reasonably implement. Unfortunately when things like this do get implemented, there is often suspicion and cries of plaintext problems.

That’s not to say that there aren’t sites that do store passwords in plaintext or symmetric encryption. Those sites are problematic, and need to get fixed. If the password history fuzziness seems too clever, such as Levenshtein or Hamming distance, then that might indicate bigger problems.