This isn't a big deal as I did this in the first place to see what would happen. I will be re-reinstalling this particular server anyways. Using a single user and no root login I changed the password to a 100 character password through an ssh connection. The password change went through. But after exiting the session and trying to login again I can no longer login with either the new 100 character password or with the old password.
Is this a bug or is there a password limit in Ubuntu?