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This paper investigates how negative emotions arising from anxious attachment can be effectively mitigated through the design of interactions and how design-supported attachment stabilization can contribute to well-being. Anxious attachment is a type of attachment that is prominent in individuals who are highly dependent on others and have lower self-esteem in interpersonal relationships (e.g., “I need constant reassurance from my partner to feel secure.”). To illustrate how interactions can be systematically designed to alleviate anxious attachment, the paper presents the development of a self- administered interactive device that supports users in the contexts of underachievement, self- depreciation, and future worries. The development process was informed by a diary study with individuals with anxious attachment that explored daily coping strategies, and a design workshop with design professionals that generated a set of design strategies. A ten-day field evaluation study showed the device’s effectiveness in alleviating negative emotions associated with anxious attachment through three aspects: facilitating explicit emotion awareness, encouraging positive self- perception, and introspecting the problems at hand. These positive effects were more pronounced when experiencing moderate and low intense negative emotions. This paper discusses implications for design practice with future research directions.