Ignore "Bad: new and old password are too similar"

Solution 1:

For me I was able to avoid this message:

Bad: new password is just a wrapped version of the old one (and a few other similar messages)

by running $sudo passwd <my_username> instead of just $ passwd

Just obviously be aware of the security implications but at least it allows it now.

Solution 2:

A workaround would be to change the old password to a random one, and change it again to a similar one. The password history is not preserved, so this should work fine.

If you need a real solution, please include the contents of your /etc/pam.d/common-password and /etc/pam.d/chpasswd (preferably using a pastebin).