The accelerated growth of the sharing economy has reshaped work, providing flexible and decentralized earnings opportunities through digital platforms like Uber, Airbnb, and Upwork. While this shift brings entrepreneurship and independence, it also subjects gig workers to extreme vulnerabilities, especially in social security. Differently from regular employees, gig workers tend to be identified as independent contractors and continue to be excluded from such important employee benefits as health insurance, retirement schemes, paid time off, and unemployment coverage. The chapter critically discusses gig worker challenges in lacking social protection and investigates international statistics that highlight the extent of benefit exclusion. Based on global reporting and local statistics, it mounts a strong argument for rethinking social security systems that fit the flexible but uncertain character of gig labor. The chapter also addresses current gaps in regulation and points out new models like portable benefits and public–private arrangements. Finally, it argues for new, flexible policy solutions that protect workers’ rights without undermining the dynamism of platform-based work. In so doing, it seeks to help shape a sustainable, fair future of work for the changing digital economy.