From: George Orwell on
> > Hi,
> >
> > If we consider a password of n characters, given the user will probably
> > likely enter only alpha characters and numbers and a small set of
> > characters like @#$ etc. how do we calculate the actual entropy of the
> > password? Thanks.
>
> entropy is a realtive number, it depends on the set and selection
> process. For example, If the attacker happens to know that the password
> used has a special meaning for the user, then the entropyis 0.
> If you assume that the letters, characters, numbers used are used
> according to their distribution in Shakespeare, you get another number.
> If you assume that the pairs of letters (q is always followed by u for
> example) still another one. There is no "entropy of the password".
> It also depends on the attacker and his procedure for doing an
> exhaustive search on the password. That is the only true measure, and of
> course, unless you know the attacker, impossible to know. So you guess,
> and your guess will be different from mine.

Let's suppose the set is alpha characters, digits, and 12 characters like
the ones from the top row of keys on your keyboard. Let's suppose the
password is n characters long and doesn't have to be a word, any
combination. I'm new to this and this isn't a trick question or if it is
it's not intentional. I'm trying to learn how this works. Can anybody give
me an idea? Just based on the simple example I asked about.....

Il mittente di questo messaggio|The sender address of this
non corrisponde ad un utente |message is not related to a real
reale ma all'indirizzo fittizio|person but to a fake address of an
di un sistema anonimizzatore |anonymous system
Per maggiori informazioni |For more info
https://www.mixmaster.it




From: unruh on
On 2010-05-23, George Orwell <nobody(a)mixmaster.it> wrote:
>> > Hi,
>> >
>> > If we consider a password of n characters, given the user will probably
>> > likely enter only alpha characters and numbers and a small set of
>> > characters like @#$ etc. how do we calculate the actual entropy of the
>> > password? Thanks.
>>
>> entropy is a realtive number, it depends on the set and selection
>> process. For example, If the attacker happens to know that the password
>> used has a special meaning for the user, then the entropyis 0.
>> If you assume that the letters, characters, numbers used are used
>> according to their distribution in Shakespeare, you get another number.
>> If you assume that the pairs of letters (q is always followed by u for
>> example) still another one. There is no "entropy of the password".
>> It also depends on the attacker and his procedure for doing an
>> exhaustive search on the password. That is the only true measure, and of
>> course, unless you know the attacker, impossible to know. So you guess,
>> and your guess will be different from mine.
>
> Let's suppose the set is alpha characters, digits, and 12 characters like
> the ones from the top row of keys on your keyboard. Let's suppose the
> password is n characters long and doesn't have to be a word, any
> combination. I'm new to this and this isn't a trick question or if it is
> it's not intentional. I'm trying to learn how this works. Can anybody give
> me an idea? Just based on the simple example I asked about.....

If yo uwant to be incredibly naive, and assume that the person ( and the
attacker) randomly (without bias) chooses each character from the 74
characters you specified (26LC, 26UC, 10 numbers and 12 characters) Then
the number of combinations of N letters is 74^N. or 2^(6.2N) different
passwords. thus the "entropy" is 6.2N bits. But of course nobody
actually picks from those 74 chacters at random and smart attackers know
this and do not attack it by going through all 74^N possiblilities.
There are all kinds of psychological biases -- lowercase letters more
prevelant than upper case, which are more prevelant than numbers which
ae more prevelant than the special characters. And a good search will be
biased in that way. dzP8 will be rarer than daly say. But at this point
figuring out what the entropy of a given password is, given the biases
in the searches, and in people's choices becomes very very difficult.

Thus for example, using your name Orwell would in theory be as rare as
any other 6 letter word, 6.4*6= 38 bits of entropy, but it is clearly
not. Given that it is your name (well lets pretend) its entropy is
probably of the order of 4 or 5 bits, not 38 bits.
As I said, entropy is a relative concept.
From: Paul Rubin on
Nomen Nescio <nobody(a)dizum.com> writes:
> If we consider a password of n characters, given the user will probably
> likely enter only alpha characters and numbers and a small set of
> characters like @#$ etc. how do we calculate the actual entropy of the
> password? Thanks.

If you mean a password supplied by the user, it is drawn from an unknown
distribution so there is no way for a program to compute or estimate the
entropy. If you want a password with known entropy, you have to
generate it from a known distribution (i.e. with an RNG) and assign it
to the user.
From: Joseph Ashwood on
"Nomen Nescio" <nobody(a)dizum.com> wrote in message
news:d43942f964b20a8fc183f1ed16cb4c2d(a)dizum.com...
> If we consider a password of n characters, given the user will probably
> likely enter only alpha characters and numbers and a small set of
> characters like @#$ etc. how do we calculate the actual entropy of the
> password? Thanks.

While a perfect number is impossible, if you have a large enough set of
users you can check the passwords against each other, this gives a
distribution for general purposes. Enough samples and you can get an
estimate of the real entropy of the password. With the list of compromised
passwords available from a few locations I immediately see much connection
between entropy and length (most common password 6 characters "123456",
second 8 characters "password").

Won't give an accurate answer until you get unlimited samples, but should
allow for a reasonably close approximation.
Joe

From: Paul Rubin on
"Joseph Ashwood" <ashwood(a)msn.com> writes:
> While a perfect number is impossible, if you have a large enough set
> of users you can check the passwords against each other, this gives a
> distribution for general purposes.

That doesn't make any sense. Each person picks a password from their
own distribution. You can't usefully treat them as being drawn from one
monstrous distribution. There's a bunch of cheesy tests you can use to
filter out obviously bad passwords, but in the end if you're running a
high-security application, you simply can't rely on passwords for
authentication. If you're running a casual web forum or the like, you
don't have to worry too much about password entropy.

Also, checking passwords against each other isn't so good since it means
you're storing them as unsalted hashes or even in the clear.