It provides a pseudo 20-character string. It’s obviously base64 from visual 
inspection, and some of the smarter crackers, like oclHashcat do base64 
transliteration.

So yeah, the added length obvious promotes some additional entropy, but I don’t 
think it’s much.

[Fun fact that I just looked up: oclHashcat has been clocked at 8 billion 
NTLMv2 hashes a second and over 14 billion SHA-256 hashes a second. Obviously 
that’s local and not over the net – but still…. Once a hacker gets that 
database full of hashes, those passwords may have a very limited lifetime.]

From: [email protected] [mailto:[email protected]] On 
Behalf Of Sean Martin
Sent: Thursday, February 4, 2016 10:53 AM
To: [email protected]
Subject: Re: [powershell] Random Password Generator

Perhaps I should explain why this particular method works for my use case. We 
got dinged on an internal audit because we have several hundred AD accounts 
whose password has not be changed in quite some time. The vast majority of 
these are shared mailbox accounts that are disabled. I used this method in a 
script to change the password for all of those disabled accounts every couple 
of months.

In regards to the article, I think I understand your math, but the example I 
provided generates a 20 character string, not 15, so how does that affect your 
calculation?

- Sean

On Wed, Feb 3, 2016 at 7:11 PM, Michael B. Smith 
<[email protected]<mailto:[email protected]>> wrote:
So, I just read the article you mentioned, and I have to tell you, I think he’s 
(or she’s) incorrect.

GetBytes() returns random bytes. That’s 0-255 taking up 8 bits. Ln2(8) = 3. 
Fifteen characters at 3 bits of entropy each will give you 45 bits of entropy. 
But then you convert it to Base64. Base64 is limited to 6 bits of information ( 
[System.Math]::Pow(2, 6) = 64 ). That is by definition where the name of the 
algorithm comes from! Ln2(6) = 2.58. Significant reduction.

He/she also conflates the fact that while a representation of Base64 is 
generally longer (although not always for small amounts of text) the entropy is 
controlled by the character set, not the representation.

If I remember correctly, the number of printable ASCII characters is actually 
only 96. Ln2(7) ~= 2.81. But the number is effectively less than that, because 
32 of those characters are not used. So Ln2(6.5) ~= 2.70.

So the maximum entropy you can obtain with a 15 character password is ~40.5 – 
assuming that the password is completely random and the available character set 
allows all 96 characters available. That’s almost 50 years to brute force. But 
the password will almost certainly be gibberish.

Note: There are assumptions in this calculation: [1] I’m assuming online 
cracking attempts, not on-premises. On-premises cracking attempts can be much 
much faster, on the order of 50 million attempts a second; [2] Yes, Windows 
will allow you to enter in non-printable characters for passwords – but very 
few websites (if any?) will allow this. In fact, most websites have far more 
strict password guidelines than “15 maximum characters of charset-96”.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]<mailto:[email protected]>] 
On Behalf Of Michael B. Smith
Sent: Wednesday, February 3, 2016 10:36 PM
To: [email protected]<mailto:[email protected]>
Subject: RE: [powershell] Random Password Generator

The maximum entropy you get from Base64 is 2.58 bits per character, kinda by 
definition( ln2( 6 ) ). Given that your maximum length is 15 digits, that 
limits you to ~38 bits of entropy. At a thousand guesses a second, that’s about 
8 years to brute force. Not bad.

However, you’ve GIVEN UP over 10 bits of entropy because of four constant 
characters, taking you to about 28 bits of entropy. Believe it or not, having 
constants makes a password far far easier to crack. (This is why the revelation 
of a non-random non-prime in netcat/socat is such a big deal – it makes 
Diffie-Helman much much simpler to crack.)

That’s about 3 days to brute force.

That is completely believable for someone to spend the time/energy to crack. 
(And remember, the 3 days assumes that your password is the last one checked, 
out of the entire “password universe” – on average, assume half that.)

So, the lesson here is that 15 bytes of base64 is fine (if impossible to 
remember). But don’t use constants. Evah.

From: [email protected]<mailto:[email protected]> 
[mailto:[email protected]] On Behalf Of Sean Martin
Sent: Wednesday, February 3, 2016 3:24 PM
To: [email protected]<mailto:[email protected]>
Subject: [powershell] Random Password Generator

I don't get the opportunity to contribute all that often so I thought I would 
throw this out there in case it helps anyone.

I got the method from this article: 
https://www.scriptjunkie.us/2013/09/secure-random-password-generation/

I modify the resulting password by prepending/appending a couple of special and 
numerical characters to ensure it meets complexity requirements in my current 
environment.

Easy way to generate a secure password whenever the need arises. Critiques are 
always welcome.

===================================================================

# Generate Random Password

$randombytes = new-object byte[] 15
(new-object 
System.Security.Cryptography.RNGCryptoServiceProvider).GetBytes($randombytes)
$pass = [System.Convert]::ToBase64String($randombytes)
$password = "&#" + $pass + "82"

Write-Host ""
Write-Host "Your password is: " -ForeGroundColor Cyan -NoNewLine
Write-Host "$Password" -ForeGroundColor Yellow
Write-Host ""
Write-Host ""
Write-Host "Press enter to exit script..." -ForeGroundColor Cyan

$Pause = Read-Host
Exit

==================================================================

- Sean

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