An automatic documentation generation and management system and method, for documenting configurable systems such as complex software applications and hardware systems is disclosed. The method retrieves configuration parameters from the configurable system and utilizes them to automatically generate an explanatory document specific to the configured system. The invention also discloses a documentation appliance system, which is a dedicated documentation server coupled to the configurable system via a communication network, preferably via an Intranet. In yet another alternative, the invention may be practiced by integrating code for automatic documentation generation within the configurable system program.