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I have an encrypted /home and just had to reinstall Ubuntu. Problem is, my /home partition is encrypted with my old password, which is short, and my new system has a new password on it. I could fix this by setting my old password on the new system, and but passwd won't allow me to change the password to something short. Is there a way to override passwd's checks?

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You can change the password as the root user for a specific user.....it might complain but allow you to do it.

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