Techniques for modification of access expiration conditions are presented. A principal supplies a password associated with establishing access to a target resource. In response to the password, characteristics of the password are examined and a custom expiration condition is generated for the password in response to the characteristics and policy. When the custom expiration condition is satisfied, the password and access to the target resource become invalid for use. Moreover, the principal may interactively change a complexity level of any proposed password for purposes of attempting to enhance the expiration condition or for purposes of attempting to degrade the expiration condition.