An active new password entry dialog provides a compact visual indication of adherence to password policies. A visual indication of progress towards meeting all applicable password policies is included in the display and updated as new password characters are being entered. A visual hint associated with at least one applicable password policy that has not yet been satisfied is also included in the display. An ability to obtain more detailed comprehensive password policy information is also permitted upon user command (e.g., including an indication whether each password policy has yet been met or unmet). Preferably the displayed hint and associated applicable password policy not yet satisfied is randomly changed during entry of a new password (e.g., upon the entry of each new password character).