This presentation begins with a brief overview of Singapore and a snapshot of the current state of mental health. It then introduces three key areas where the Health Promotion Board (HPB) leverages the digital space to promote mental well-being: (a) enhancing mental health literacy, (b) improving coping ability through self-directed activities, and (c) upskilling individuals to support others. This presentation will focus specifically on the second area, which is improving coping ability through self-directed activities, while the other two areas will be covered in a separate presentation. The first initiative covered is Healthy 365, a free mobile app developed by HPB to encourage healthier lifestyles through tracking features, gamification, and rewards, with about 45 per cent of Singaporean adults using it as of 31 December 2024. Within the app, the Sleep Challenge encourages users to improve their sleep hygiene. The presentation will explore how the challenge was first piloted and later enhanced using behavioural science, key user insights and learnings, and its evolution from periodic campaigns to an always-on format supported by Smart Automated Nudges and upcoming weekly lifestyle quests. The second initiative is LumiHealth, a collaboration between HPB and Apple that uses curated health challenges, activity coaching, and rewards to guide users toward healthier habits, including mental well-being. Accessible via iPhone and enhanced with Apple Watch features, LumiHealth had over 226,000 activated users by the end of 2024. Examples of mental well-being quests such as those promoting positivity, gratitude, and social connection will be shared. The presentation concludes by summarising insights from both platforms and reflecting on how self-directed, tech-enabled tools can strengthen mental well-being in Singapore, along with future opportunities for scaling these efforts.