A slightly different way to generate strong, memorable passwords

It’s a good idea to avoid remembering passwords – the more passwords you need to remember, the more tempting it is to re-use them. Ideally you should use a password manager like Bitwarden to store almost all of your passwords.

But of course you can’t store your Bitwarden password in Bitwarden, so it’s still necessary to memorize at least that one password. You’ll probably also need to memorize your disk encryption password and your user account password for your computer. So how do you choose these passwords to be secure and memorable?

Entropy

If you’re interested in computer security, you have probably seen the “Correct Horse Battery Staple” XKCD comic. It advocates choosing four random common words as your passphrase, instead of doing the traditional password generation black magic, because these passwords can be harder to guess and easier to remember. It’s a good illustration of the concept of “entropy”: In the context of security, entropy is a measure of how difficult your password is to guess, and it depends on how you chose the password.

For example, If you choose your password by flipping a coin 10 times, and adding a “1” if you get heads or a “0” if you get tails, your password has 10 bits of entropy. That means that an attacker who knew your decision procedure would have to guess, on average, 2^(10-1) passwords in order to successfully guess the one you chose. Adding one bit of entropy (one coin flip) to your password doubles the number of guesses required. It’s a good idea to incorporate as many truly random choices into your password as possible, to ensure that it’s really unpredictable.

Diceware

A respected way to generate secure passwords is by using the Diceware word list. You sit there rolling dice for a few minutes to choose random words. If you want your password to have 128 bits of entropy (enough for essentially all purposes), you can generate one by randomly choosing ten words from the Diceware list. And if you roll a password with N words in it, you’ll end up with N * log2(6^5) bits of entropy.

I’ve used this method in the past, and it works well. But the passwords I get are often difficult to remember: The words don’t have any semantic structure, and it’s not always easy to come up with mnemonics for lists of ten words.

The Reordered Diceware method

Instead of choosing N words in order and trying to remember them in the order you rolled them, you might try reordering the words you roll, to give them a more memorable structure. Unfortunately you lose some bits when doing this, and it’s important to take that into account. Pessimistically, your password using this method could have as few as log2(6^5 choose N) bits of entropy, or 107 bits for 10 words. To guarantee more than 128 bits of entropy, now your password needs to contain 13 words. And you’re still stuck using all the words you rolled, which limits how memorable your password will be.

Reordered Diceware with discards

I’ve started generating passwords in the following way:

First, roll 15 Diceware words. Then, choose your favorite 13 of those 15 words, and discard the other 2. Put those 13 words into any order you want, with punctuation separating them. This password can be very memorable, because you had a lot of options for just how it should be put together. And while the precise entropy is difficult to calculate, I believe it is at least 127.75 bits no matter how you choose the discards and ordering. For more details about how to compute this lower bound for different password sizes, check out Marcello Herreshoff’s solution here.

In addition to being strong, I’ve found that passwords generated this way are quite memorable, compared to the pure Diceware method.

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