Almost 60,000 people claimed asylum at Canada's border with the United States between 2017 and 2020, marking Canada's first sustained cross-border asylum migration since the 1990s. Virtually, all entered irregularly via a rural road on the New York/Québec border. The “Roxham Road route” was partly owing to the 2004 Canada/US Safe Third Country Agreement (STCA), which allows both states to refuse asylum-seekers on the grounds that the other offers commensurate protection standards yet only applies to official ports of entry. Roughly, 40 percent of the 60,000 who claimed asylum were US residents with precarious immigration status. This article examines the route's emergence and contributes a novel case on decision-making and destination choices for asylum migration. Data are derived from interviews with over 300 asylum-seekers, two dozen experts, and monthly asylum statistics. The central finding is that Trump-administration immigration policies were the major driver for asylum migration yet do not entirely explain the new route, since a relatively small number of US residents departed for Canada. Interviews revealed that while Trump-era policies fostered a climate of fear, individual experiences with immigration enforcement, loss of temporary protected status, or deferred asylum cases were catalysts for migration. Welcoming Canadian rhetoric and liberal asylum policies were only considered in light of risk in the United States, challenging research findings that asylum-seekers are primarily motivated by destination-state policies. The article also offers qualitative methods for connecting asylum data with migrant decision-making and problematizes the STCA's ethics and effectiveness for managing asylum.