Despite its ubiquity, the trucking industry is not well-understood in social scientific literature. Gathering insight into truckers’ worlds is difficult due to the solitary, isolating, and unpredictable nature of the work. An understanding of truckers’ work lives and work ideologies is even further limited. When an outsider engages in participant observational over-the-road fieldwork, the boundaries of traditional research relationships are called into question. The intensity of this research milieu, however—both the truckers’ workplace and their home on the road—allows the researcher to observe first-hand, and in real time, myriad hidden stressors that truck drivers confront as well as the strategies they employ to mitigate this tension. In this paper, I examine three challenging dimensions of over-the-road participant observational research with truck drivers: (A) managing access within drivers’ work lives, (B) managing trust and reciprocity within drivers’ work ideologies, and (C) contextualizing professional boundaries. Finally, I discuss the strategies I employed to ensure ethical research amidst the uncertain intimacy of the truckers’ worlds I temporarily inhabited.