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Add a password entropy meter to Users. Calculate the zero-order entropy of the string, and give the user a poor/weak/good/strong/secure rating.
Also, use a list of the top 100,000 most common passwords and ban them, as it doesn't matter how much entropy your password has if it's the word "password".
References:
- https://www.grc.com/haystack.htm
- http://arstechnica.com/security/2013/05/its-official-password-strength-meters-arent-security-theater/
- http://en.wikipedia.org/wiki/Entropy_%28information_theory%29
- http://blog.shay.co/password-entropy/
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