The gig economy has transformed the service industry by offering flexible work opportunities, with food delivery platforms playing a key role in the sharing economy. However, delivery partners face significant risks due to the lack of formal employment protections. While some platforms provide episodic benefits like accident insurance and financial incentives to improve retention, their effectiveness in safeguarding riders remains uncertain. This study examines the challenges delivery partners encounter in accessing safety measures, awareness towards free basic insurance and the barriers to adopting premium insurance. The findings highlight how digital platforms, including Grab, Foodpanda, and Lalamove, implement benefits to retain delivery partners through strategic incentives and safety measures. Although free basic insurance is widely available, the uptake of premium insurance remains low due to inconsistent earnings, limited awareness, and concerns over claim processes. Financial stability, perceived necessity, and trust in claims influence a rider’s willingness to invest in protection. Despite incentives and safety measures, riders continue to face high risks, income instability, and lack of social security coverage, raising concerns about their long-term well-being. This study underscores the need for greater transparency, better insurance accessibility, and structured regulatory frameworks. An equitable approach integrating short-term benefits with long-term security initiatives is crucial for sustaining commitment and fostering a fairer gig economy.