The study delves into the complex phenomenon of pickpocketing, a global affliction that persists across nations like India, posing a familiar threat to individuals in crowded spaces. Despite its historical roots as an opportunistic crime, pickpocketing has evolved into an organized enterprise, often involving economically disadvantaged individuals forming groups. While prevalent in major cities worldwide, pickpocketing lacks explicit legal recognition in India's Penal Code, falling under broader theft laws. Leveraging data from automated fare collection systems and trajectory analysis, this research refines anomaly-detection applications to identify suspicious behaviors, shedding light on the environmental factors shaping pickpocketing trends. The study focuses on the social considerations of pickpocketing in Kolkata, India, exploring victim experiences and perceptions. Findings reveal the broader social impacts of pickpocketing, beyond just financial loss, with victims enduring significant social and psychological distress. Despite lacking specific legal penalties, pickpocketing remains a prevalent issue, highlighting the need for collective efforts from governments, law enforcement, and the public to combat it effectively.