HOWTO: Generating Many Good Random Passwords 'Automagically' using Bash

Scenario I:  Creating reasonably complicated passwords for a school (for an entire student body):

"Printers are lame and people can't read.  What that means is we cannot use the number zero or the capital letter O.  We cannot use the number one, the letter l "el", or the capital I "i".  Long passwords are harder to learn so we will limit ours to six characters.  It is also nice to limit this to all lowercase letters because kids get confused whenever caps-lock has a chance of accidentally getting turned on."

#!/bin/bash
#
# Script to generate X passwords and 'tee'
# the results to a file named passwords.txt
#
X=1000
i=1
while [ $i -le $X ]
do
    head -c 500 /dev/urandom | tr -dc a-hj-km-npr-z2-9 \
        | head -c 6 | tee -a passwords.txt;
        echo | tee -a passwords.txt;
    let "i+=1"
done

Sample passwords from this solution (what they'll look like):

39uy9n
h52bx7
m6agtz
6cmbwj


Scenario II: Creating complex passwords for a company/business/school/home-use with strict password requirements.

"All letters.  Upper and lower case.  All digits.  Length must be at least ten characters. Guarantee: passwords will end up on sticky notes."

#!/bin/bash
#
# Script to generate X passwords and 'tee'
# the results to a file named passwords.txt
#
X=1000
LENGTH=10
i=1
while [ $i -le $X ]
do
    head -c 500 /dev/urandom | tr -dc a-zA-Z0-9 \
        | head -c $LENGTH | tee -a passwords.txt;
        echo | tee -a passwords.txt;
    let "i+=1"
done

Sample passwords from this solution (what they'll look like):

co3Jr0uEKg
SPIuKLMk7h
C69OsDVbyc
XFkdNK7Hfa


Scenario III: Creating passwords for a company/business/school/home-use with an anal-retentive network admin.

"Super long and complex passwords with special characters like #%^*&!. and so on.  Guarantee: passwords will end up on sticky notes."

#!/bin/bash
#
# Script to generate X passwords and 'tee'
# the results to a file named passwords.txt
#
X=1000
LENGTH=16
SEED=1000
i=1
while [ $i -le $X ]
do
    head -c $SEED /dev/urandom | tr -dc [:punct:]a-zA-Z0-9 \
        | head -c $LENGTH | tee -a passwords.txt;
        echo | tee -a passwords.txt;
    let "i+=1"
done

Sample passwords from this solution (what they'll look like):

Nb9|2Cb$LT;,=t-4
([[Y?#>VH]_c%fEU
qv-_)x#nU+OEyav&
e~fZ@<}2'2a|)TGV


The ultra paranoid should take a look at The Diceware Passphrase Home Page for more information on actually using one or more dice to generate a password (a.k.a., passphrase).  From the Diceware web-site:  "Diceware is a method for picking passphrases that uses dice to select words at random from a special list called the Diceware Word List. Each word in the list is preceded by a five digit number. All the digits are between one and six, allowing you to use the outcomes of five dice rolls to select one unique word from the list."

Special thanks to Larry Steinke for providing the motivation and tips to prepare this post.  Special thanks to Tim Freeman for providing the initial tip on using /dev/urandom to generate passwords, and for the pointer to Diceware.