Adopting the “heroic mood” is a method of Singerian inquiring systems (Churchman, 1971) that promotes the discovery of new knowledge by expedition. The heroic mood fortifies and encourages an inquirer to embark upon a purposeful journey that critically examines the status quo and leads the way to novel solutions. However, if an inquirer adopts the heroic mood, what prevents this adventurer from losing control of the inquiry process and hindering the free inquiry of others? Along with the knowledge-seeking maneuvers emboldened by the heroic mood come risks. This research asks what guidelines should be designed into a knowledge management system to aid a Singerian inquirer’s assessment of liberty, both the inquirer’s liberty and the liberty of others. A tentative set of five guidelines for the design of liberty support are derived from the stories of five early American patriots who performed knowledge tasks in the ethically challenging conditions of social revolution.