1. What makes a good password?
  2. Generating secure passwords
  3. Generating security tokens
  4. Conclusion

Passwords are used everywhere in our modern life. Between your email account and your bank card, a lot of critical security infrastructure relies on "something you know", a password. Yet there is little standard documentation on how to generate good passwords. There are some interesting possibilities for doing so; this article will look at what makes a good password and some tools that can be used to generate them.

There is growing concern that our dependence on passwords poses a fundamental security flaw. For example, passwords rely on humans, who can be coerced to reveal secret information. Furthermore, passwords are "replayable": if your password is revealed or stolen, anyone can impersonate you to get access to your most critical assets. Therefore, major organizations are trying to move away from single password authentication. Google, for example, is enforcing two factor authentication for its employees and is considering abandoning passwords on phones as well, although we have yet to see that controversial change implemented.

Yet passwords are still here and are likely to stick around for a long time until we figure out a better alternative. Note that in this article I use the word "password" instead of "PIN" or "passphrase", which all roughly mean the same thing: a small piece of text that users provide to prove their identity.

What makes a good password?

A "good password" may mean different things to different people. I will assert that a good password has the following properties:

High entropy means that the password should be unpredictable to an attacker, for all practical purposes. It is tempting (and not uncommon) to choose a password based on something else that you know, but unfortunately those choices are likely to be guessable, no matter how "secret" you believe it is. Yes, with enough effort, an attacker can figure out your birthday, the name of your first lover, your mother's maiden name, where you were last summer, or other secrets people think they have.

The only solution here is to use a password randomly generated with enough randomness or "entropy" that brute-forcing the password will be practically infeasible. Considering that a modern off-the-shelf graphics card can guess millions of passwords per second using freely available software like hashcat, the typical requirement of "8 characters" is not considered enough anymore. With proper hardware, a powerful rig can crack such passwords offline within about a day. Even though a recent US National Institute of Standards and Technology (NIST) draft still recommends a minimum of eight characters, we now more often hear recommendations of twelve characters or fourteen characters.

A password should also be easily "transferable". Some characters, like & or !, have special meaning on the web or the shell and can wreak havoc when transferred. Certain software also has policies of refusing (or requiring!) some special characters exactly for that reason. Weird characters also make it harder for humans to communicate passwords across voice channels or different cultural backgrounds. In a more extreme example, the popular Signal software even resorted to using only digits to transfer key fingerprints. They outlined that numbers are "easy to localize" (as opposed to words, which are language-specific) and "visually distinct".

But the critical piece is the "memorable" part: it is trivial to generate a random string of characters, but those passwords are hard for humans to remember. As xkcd noted, "through 20 years of effort, we've successfully trained everyone to use passwords that are hard for human to remember but easy for computers to guess". It explains how a series of words is a better password than a single word with some characters replaced.

Obviously, you should not need to remember all passwords. Indeed, you may store some in password managers (which we'll look at in another article) or write them down in your wallet. In those cases, what you need is not a password, but something I would rather call a "token", or, as Debian Developer Daniel Kahn Gillmor (dkg) said in a private email, a "high entropy, compact, and transferable string". Certain APIs are specifically crafted to use tokens. OAuth, for example, generates "access tokens" that are random strings that give access to services. But in our discussion, we'll use the term "token" in a broader sense.

Notice how we removed the "memorable" property and added the "compact" one: we want to efficiently convert the most entropy into the shortest password possible, to work around possibly limiting password policies. For example, some bank cards only allow 5-digit security PINs and most web sites have an upper limit in the password length. The "compact" property applies less to "passwords" than tokens, because I assume that you will only use a password in select places: your password manager, SSH and OpenPGP keys, your computer login, and encryption keys. Everything else should be in a password manager. Those tools are generally under your control and should allow large enough passwords that the compact property is not particularly important.

Generating secure passwords

We'll look now at how to generate a strong, transferable, and memorable password. These are most likely the passwords you will deal with most of the time, as security tokens used in other settings should actually never show up on screen: they should be copy-pasted or automatically typed in forms. The password generators described here are all operated from the command line. Password managers often have embedded password generators, but usually don't provide an easy way to generate a password for the vault itself.

The previously mentioned xkcd cartoon is probably a common cultural reference in the security crowd and I often use it to explain how to choose a good passphrase. It turns out that someone actually implemented xkcd author Randall Munroe's suggestion into a program called xkcdpass:

    $ xkcdpass
    estop mixing edelweiss conduct rejoin flexitime

In verbose mode, it will show the actual entropy of the generated passphrase:

    $ xkcdpass -V
    The supplied word list is located at /usr/lib/python3/dist-packages/xkcdpass/static/default.txt.
    Your word list contains 38271 words, or 2^15.22 words.
    A 6 word password from this list will have roughly 91 (15.22 * 6) bits of entropy,
    assuming truly random word selection.
    estop mixing edelweiss conduct rejoin flexitime

Note that the above password has 91 bits of entropy, which is about what a fifteen-character password would have, if chosen at random from uppercase, lowercase, digits, and ten symbols:

    log2((26 + 26 + 10 + 10)^15) = approx. 92.548875

It's also interesting to note that this is closer to the entropy of a fifteen-letter base64 encoded password: since each character is six bits, you end up with 90 bits of entropy. xkcdpass is scriptable and easy to use. You can also customize the word list, separators, and so on with different command-line options. By default, xkcdpass uses the 2 of 12 word list from 12 dicts, which is not specifically geared toward password generation but has been curated for "common words" and words of different sizes.

Another option is the diceware system. Diceware works by having a word list in which you look up words based on dice rolls. For example, rolling the five dice "1 4 2 1 4" would give the word "bilge". By rolling those dice five times, you generate a five word password that is both memorable and random. Since paper and dice do not seem to be popular anymore, someone wrote that as an actual program, aptly called diceware. It works in a similar fashion, except that passwords are not space separated by default:

    $ diceware

Diceware can obviously change the output to look similar to xkcdpass, but can also accept actual dice rolls for those who do not trust their computer's entropy source:

    $ diceware -d ' ' -r realdice -w en_orig
    Please roll 5 dice (or a single dice 5 times).
    What number shows dice number 1? 4
    What number shows dice number 2? 2
    What number shows dice number 3? 6
    Aspire O's Ester Court Born Pk

The diceware software ships with a few word lists, and the default list has been deliberately created for generating passwords. It is derived from the standard diceware list with additions from the SecureDrop project. Diceware ships with the EFF word list that has words chosen for better recognition, but it is not enabled by default, even though diceware recommends using it when generating passwords with dice. That is because the EFF list was added later on. The project is currently considering making the EFF list be the default.

One disadvantage of diceware is that it doesn't actually show how much entropy the generated password has — those interested need to compute it for themselves. The actual number depends on the word list: the default word list has 13 bits of entropy per word (since it is exactly 8192 words long), which means the default 6 word passwords have 78 bits of entropy:

    log2(8192) * 6 = 78

Both of these programs are rather new, having, for example, entered Debian only after the last stable release, so they may not be directly available for your distribution. The manual diceware method, of course, only needs a set of dice and a word list, so that is much more portable, and both the diceware and xkcdpass programs can be installed through pip. However, if this is all too complicated, you can take a look at Openwall's passwdqc, which is older and more widely available. It generates more memorable passphrases while at the same time allowing for better control over the level of entropy:

    $ pwqgen
    $ pwqgen random=78

For some reason, passwdqc restricts the entropy of passwords between the bounds of 24 and 85 bits. That tool is also much less customizable than the other two: what you see here is pretty much what you get. The 4096-word list is also hardcoded in the C source code; it comes from a Usenet sci.crypt posting from 1997.

A key feature of xkcdpass and diceware is that you can craft your own word list, which can make dictionary-based attacks harder. Indeed, with such word-based password generators, the only viable way to crack those passwords is to use dictionary attacks, because the password is so long that character-based exhaustive searches are not workable, since they would take centuries to complete. Changing from the default dictionary therefore brings some advantage against attackers. This may be yet another "security through obscurity" procedure, however: a naive approach may be to use a dictionary localized to your native language (for example, in my case, French), but that would deter only an attacker that doesn't do basic research about you, so that advantage is quickly lost to determined attackers.

One should also note that the entropy of the password doesn't depend on which word list is chosen, only its length. Furthermore, a larger dictionary only expands the search space logarithmically; in other words, doubling the word-list length only adds a single bit of entropy. It is actually much better to add a word to your password than words to the word list that generates it.

Generating security tokens

As mentioned before, most password managers feature a way to generate strong security tokens, with different policies (symbols or not, length, etc). In general, you should use your password manager's password-generation functionality to generate tokens for sites you visit. But how are those functionalities implemented and what can you do if your password manager (for example, Firefox's master password feature) does not actually generate passwords for you?

pass, the standard UNIX password manager, delegates this task to the widely known pwgen program. It turns out that pwgen has a pretty bad track record for security issues, especially in the default "phoneme" mode, which generates non-uniformly distributed passwords. While pass uses the more "secure" -s mode, I figured it was worth removing that option to discourage the use of pwgen in the default mode. I made a trivial patch to pass so that it generates passwords correctly on its own. The gory details are in this email. It turns out that there are lots of ways to skin this particular cat. I was suggesting the following pipeline to generate the password:

    head -c $entropy /dev/random | base64 | tr -d '\n='

The above command reads a certain number of bytes from the kernel (head -c $entropy /dev/random) encodes that using the base64 algorithm and strips out the trailing equal sign and newlines (for large passwords). This is what Gillmor described as a "high-entropy compact printable/transferable string". The priority, in this case, is to have a token that is as compact as possible with the given entropy, while at the same time using a character set that should cause as little trouble as possible on sites that restrict the characters you can use. Gillmor is a co-maintainer of the Assword password manager, which chose base64 because it is widely available and understood and only takes up 33% more space than the original 8-bit binary encoding. After a lengthy discussion, the pass maintainer, Jason A. Donenfeld, chose the following pipeline:

    read -r -n $length pass < <(LC_ALL=C tr -dc "$characters" < /dev/urandom)

The above is similar, except it uses tr to directly to read characters from the kernel, and selects a certain set of characters ($characters) that is defined earlier as consisting of [:alnum:] for letters and digits and [:graph:] for symbols, depending on the user's configuration. Then the read command extracts the chosen number of characters from the output and stores the result in the pass variable. A participant on the mailing list, Brian Candler, has argued that this wastes entropy as the use of tr discards bits from /dev/urandom with little gain in entropy when compared to base64. But in the end, the maintainer argued that reading "reading from /dev/urandom has no [effect] on /proc/sys/kernel/random/entropy_avail on Linux" and dismissed the objection.

Another password manager, KeePass uses its own routines to generate tokens, but the procedure is the same: read from the kernel's entropy source (and user-generated sources in case of KeePass) and transform that data into a transferable string.


While there are many aspects to password management, we have focused on different techniques for users and developers to generate secure but also usable passwords. Generating a strong yet memorable password is not a trivial problem as the security vulnerabilities of the pwgen software showed. Furthermore, left to their own devices, users will generate passwords that can be easily guessed by a skilled attacker, especially if they can profile the user. It is therefore essential we provide easy tools for users to generate strong passwords and encourage them to store secure tokens in password managers.

Note: this article first appeared in the Linux Weekly News.

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