Context: In this empirical and conceptual paper on the historical, philosophical, and epistemological backgrounds of second-order cybernetics, the emergence of a significant pedagogical component to Heinz von Foerster’s work during the last years of the Biological Computer Laboratory is placed against the backdrop of social and intellectual movements on the American landscape. Problem: Previous discussion in this regard has focused largely on the student radicalism of the later 1960s. A wider-angled view of the American intellectual counterculture is needed. However, this historical nexus is complicated and more often dismissed than brought into clear focus. Method: This essay assembles a historical sequence of archival materials for critical analysis, linked to a conceptual argument eliciting from those materials the second-order cybernetic concepts of observation, recursion, and paradox. Results: In this period, von Foerster found the “positive of the negative” in the social and intellectual unrest of that moment and cultivated those insights for the broader constitution of a new cognitive orientation. Implications: As a successful student of his own continuing course on heuristics, von Foerster left the academic mainstream to ally his constructivist epistemology with the systems counterculture.