It is yet unclear what the root cause of this issue is - libpam, crypt,
passwd and sudo seem like primary suspects. The 256 character password
is hashed to a value which still allows a TTY login to succeed. Also,
passwd run by a different user in the context of the affected user
(using sudo) still works. So apparently it only breaks for the logged-in
user. This may help identify the root cause.

pam_unix(8) (on bionic) states:
  The maximum length of a password supported by the pam_unix module via the
  helper binary is PAM_MAX_RESP_SIZE - currently 512 bytes. The rest of the
  password provided by the conversation function to the module will be 
  ignored.

Regarding passwd, I was told this on IRC:
  passwd uses getpass() to read the password from the user, and testing just 
  getpass() alone shows it will return up to 4095 bytes long (i.e. truncates 
  at that length).

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https://bugs.launchpad.net/bugs/1822736

Title:
  Passwords longer than 255 characters break authentication

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