Chronic academic procrastination among senior high school students is increasingly understood as a self-regulatory problem involving interconnected cognitive, emotional, and interpersonal processes rather than merely poor time management. This study aimed to explore the psychological dynamics and coping mechanisms of students experiencing chronic academic procrastination. A qualitative case-study design was employed involving two eleventh-grade students purposively identified as exhibiting persistent academic task delay across multiple subjects. Supporting data were obtained from four informants consisting of a homeroom teacher, a subject teacher, a guidance-and-counseling teacher, and a peer. Data were collected through semi-structured interviews, non-participant observation, and documentation and analyzed using the interactive model of data collection, data reduction, data display, and conclusion drawing. The findings revealed a recurring psychological cycle involving negative task appraisal, low confidence, academic anxiety, guilt, fear of failure, and avoidance of academic accountability. Interpersonal relationships played an ambivalent role, functioning both as sources of distraction and social support. Students predominantly relied on maladaptive emotion-focused coping, including digital distraction, social interaction, avoidance, and other activities that provided temporary emotional relief but reinforced continued task postponement. Problem-focused strategies, such as help-seeking and task prioritization, were present but inconsistently applied. These findings highlight the importance of guidance-and-counseling interventions that integrate self-efficacy development, emotion regulation, cognitive restructuring, and adaptive coping skills rather than relying solely on time-management training.