This critical essay focuses on how British colonial institutions adversely affected the adult male character of Little Chandler in “A Little Cloud.” Having passed through two distinct masculine crises in his childhood and adolescence, Chandler is now experiencing the adult crisis of conformity to the roles society has designated for him, such as father, husband, employee, and Irish man. Throughout the story, Chandler is forced with confronting and questioning the inadequacies of these social roles, and awakens to the fact that he is trapped in these roles for life. Joyce employs this masculine crisis to awaken the Irish people to the reasons for their own subjugation, but also to prevent the male characters from passing this on to their sons, reconfirming the cyclic destruction of colonialism.