Use PAM's cracklib module on the "passwd" command. That's what it's for.

On Ubuntu, should involve uncommenting the following line in /etc/pam.d
/common-password:

# password required       pam_cracklib.so retry=3 minlen=6 difok=3

Definitely not a ssh bug (ssh should not be in the business of locking
users out because their password isn't great), so I'm going to close
this out, unless someone can find (a) a reason this is a bug, and (b) a
target for it (or assign to Ubuntu).

-- 
Small password should not log in
https://bugs.launchpad.net/bugs/31969
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