We got a number of submissions pointing to today's XKCD cartoon [1] . I think the cartoon is great, and illustrates a nice dilemma in password security. Yes, I know passwords don't work, but we still all use them and we still have to come up with reasonable passwords.

Even if you are using a password safe tool that comes up with new random passwords for each application and website, you still need to remember the password for the password safe, and there are a few applications (e.g. logging in to your system) that can't be covered by a password safe.

The basic dilemma is that you need to come up with a password that is hard to guess for others but easy enough for you to remember. Most password policies try to enforce a hard to guess password by forcing you to extend the range of characters from which you pick (different case letters, numbers, special characters). However, in real life, this may actually reduce the space of "memorable" passwords, or the total number of possible passwords.

Pass phrases, as suggested by the cartoon, are one solution. But once an attacker knows that you use a pass phrase, the key space is all for sudden limited again. There has been some research showing that a library of 3 word phrases pulled from wikipedia makes a decent dictionary to crack these passwords.

The qualify of a password is usually expressed in "bits of entropy". The "bits of entropy" are calculated by the number of bits it would take to represent all possible passwords. Lets look at some common schemes:

a 4 digit PIN: 10,000 possible passwords, or 13.3 bits (ln2(10,000)=13.3)
12 characters using the full 95 characters ASCII set: 5.4 10^23, or 78.8 bits. (this is the current NIST recommendation)

Pass phrases are harder to evaluate. It depends on the size of the vocabulary of the user, and of course the constraints of grammar. People will likely not choose some random words, but a phrase that makes some sense to them. One model that can be used to obtain a passphrase is called "Diceware", but it assumes random phrases from 6^5 words (7,776).If you consider Diceware's 7,776 words, you would need 6 words to arrive at the same 77.5 bits, close to strength that NIST asks for.

 What it all comes down to: How are people actually selecting passwords? People make pretty bad random number generators, in particular if you ask them to remember the result. A good password cracking algorithm takes this into account and tailors the password list based on password requirements and the targets background. For example, for web application pen testing, the simple ruby script "cewl" will create a custom password list from words it finds on the targets website. In past tests, I was easily able to double my password cracking success using this technique if compared to normal dictionaries.

In order to solve this, we need to figure out what passwords people really use. How about asking them for their password and offering them a candy bar in return :). And then there is always another XKCD cartoon for you [2]

[1] http://www.xkcd.org/936/
[2] http://xkcd.com/538/

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Johannes B. Ullrich, Ph.D.
SANS Technology Institute
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