This project critically examines Snapchat as a media and messaging platform that, through its design, encourages irresponsible digital behavior—such as data clutter, oversharing of intimate content, and lack of safety measures. Using heuristic evaluation, the study analyzes Snapchat’s visual language, features, and their impact on user culture. Based on these insights, new “cautious checkpoint” features were designed and tested through user studies and focus groups to promote responsible behavior without driving users away from the platform. The qualitative inquiry revealed that technological issues cannot be resolved solely through design changes; user behavior and emotional instincts must also be addressed. The project further highlighted gender-related biases influencing acceptance of new features and emphasized that awareness alone is insufficient—effective change requires intrinsic and extrinsic motivations beyond the technological realm.