Global and Individual Option to have password history be automatically cleared

Why clear the history in the first place? Presuming you follow good password practices by not reusing passwords, what is the security risk with keeping a historical record of the old values?

I have encountered three scenarios where destroying old passwords would have left me in the lurch:

  1. The password-change mechanism silently fails and I do not notice until the next login.
  2. The server suffered a failure and needed to be restored to yesterday’s backup. Those that changed their password this morning need to know their old password.
  3. If I change my work password and my laptop is at home, it continues to use the old password until I bring it into the office so that it can sync with Active Directory.

I get that “one” old password may be enough, but I have had times where my new work password was not accepted so I had to select a new one moments later — meaning that the laptop would need the 2x old password.