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Some common conceptions of Buddhist meditative practice emphasize the elimination of emotion and desire in the interest of attaining tranquility and spiritual perfection. But to place too strong an emphasis on this is to miss an important social element emphasized by major figures in the Mahāyāna and Chan/Zen Buddhist traditions who are critical of these quietistic elements and who stress instead an understanding of an enlightenment that emphasizes enriched sociality and flexible readiness to engage, and not avoid, life’s fluctuations in fortune and essential impermanence. It is argued here that these criticisms of quietism are bolstered by recent advances in the philosophy and psychology of the emotions that highlight the role of emotions in framing the context of decision making—that is, in sorting out the relevant from the irrelevant, identifying salience, and directing decisions when uncertainty prevents definitive judgment. This research makes clearer why self-liberation is fundamentally a matter of liberation from judgmental habit and inflexibility, and lends support to a view of enlightenment that emphasizes compassionate engagement with others. It also provides for a more plausible picture of the cognitive transformation involved in liberation and sheds light on the rationale for certain traditional Chan and Zen teaching tactics, such as those involving koan introspection.