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This article investigated the complex interplay of choice, socioeconomic structural factors, and empowerment influencing engagement in sex work. The analysis was focused on pathways into and reasons for staying in sex work from in-depth qualitative interviews with participants (n = 37) recruited from the Durbar community-led structural intervention in Kolkata, India. Kabeer’s theory of empowerment focused on resources, agency, and achievements was utilized to interpret the results. Results identified that contexts of disempowerment constraining resources and agency set the stage for initiating sex work, typically due to familial poverty, loss of a father or husband as a breadwinner, and lack of economic opportunities for women in India. Labor force participation in informal sectors was common, specifically in domestic, construction, and manufacturing work, but was typically insufficient to provide for families …