Removed from the roadsides by waves of “city cleaning” in the early 2000s, Kenyan crafts traders have spent their careers struggling for market access within the port city and tourism hub of Mombasa. An Indian Ocean city in which the mobile and immobile of the global economy converge and interact, some Kenyan traders strive to “jump scales” into international networks, made more possible in the last decade with the help of digital technologies such as cell phones and e‐mail. Based on research conducted between 2001 and 2014, this article explores the stories of two Kenyan crafts traders and how they negotiate the changing relationships and risks of different types of mobility, from everyday travel around Mombasa and Kenya to the mobility made possible by new telecommunication technologies. I focus on emergent strategies for economic advancement and the need to negotiate a variety of formal and informal political, legal, and economic barriers. I demonstrate that translating the new forms of digital technologies and mobility into economic success is contingent on the types of risks accompanying these new mobilities and the capacity for individuals’ social networks to help in gaining access to jobs, land, and new social connections.