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The development of the online illegal consumption market raises crucial concerns regarding online safety. This study explores the impact of such digitization on the underground employment market, specifically focusing on older triad members who use drugs in Hong Kong. Through in-depth interviews with 101 participants between 2019 and 2025, the research examines how these individuals, once active participants in the underground economy, face increasing social exclusion due to aging and rapid industry transformations since the 2000s. The findings highlight digitization of the sex, drug, and gambling industries, emphasizing the rise of online platforms that facilitate service promotion and delivery. This shift leads to the decline of traditional employment opportunities such as pimps, lookouts, and bouncers. As younger, more technologically adept individuals enter the market, older drug users struggle to adapt, encountering competency discrimination and diminishing respect. Consequently, many participants are pushed toward the more risky "arrest avoidance market," where they leverage their unique experiences to navigate the complexities of law enforcement. This paper contributes to the understanding of the intersection between aging, digitization, and the evolving nature of underground economies, shedding light on the resilience and adaptability of marginalized individuals within illicit markets.