Men sex workers in Vancouver have largely transitioned from street to online solicitation coinciding with losing "Boystown," the main outdoor sex work stroll for men. This article explores strategies and barriers to increase safety among men and trans sex workers and clients of men in Vancouver, Canada. Qualitative interviews were conducted (2012-2013) with 61 self-identifed men who currently buy and/or sell sex in a community-based research project known as CHAPS (Community Health Assessment of Men Who Purchase and Sell Sex). Drawing on a socioecological framework, thematic analysis of interview transcripts was conducted utilizing ATLAS.ti 7 software among men (39 workers; 8 buyers). Narratives indicate that gentrification and urban planning led to social isolation and loss of social support networks among men in the sex industry. Concurrently, the restructuring of sex work to online increased workers’ safety and control. Narratives reveal how the Internet can provide greater opportunities to negotiate terms of sex work and enhanced screening using webcams, reducing risks of violence, stigma, and police harassment for both workers and clients compared with the street. This study highlights how losing Boystown led to a loss of community and solidarity: key protective measures for sex workers. Online solicitation increased workers’ capacity to screen prospective clients and prevent violence. Recent legal reforms in Canada to further criminalize sex work raise significant concern for human rights and health of individuals in the sex industry, and point to the critical need to include voices of men and trans sex workers and buyers in policy discussions.