The 90-90-90 strategy from the Joint United Nations Programme on HIV/AIDS (UNAIDS) to end the AIDS epidemic by 2020 includes, as its first goal, to have 90% of all people living with HIV to know their status. Achieving this goal will depend on effectively reaching high risk populations, which include mobile populations such as truck drivers. This study aimed to characterise a sample of 305 truck drivers recruited from 2 roadside wellness clinics in Kenya in terms of anticipated HIV stigma, self-efficacy, fatalism, gender equity, sensation seeking, and self-esteem, and then determine the association of these psychosocial characteristics with HIV testing behaviour. Greater general self-efficacy was associated with higher income and more years working as a truck driver. Greater fatalism was associated with non-Christian religion, being married, and having a lower income. Greater gender equity was associated with completing high school, being married, and having higher income. Greater sensation seeking was associated with lower income and fewer years employed as a truck driver. In multivariable logistic regression adjusted for demographic variables, anticipated HIV stigma was negatively associated with having ever tested for HIV (adjusted odds ratio [aOR] = 0.79; 95% confidence interval [CI] = 0.63-0.98; p = 0.034) and self-esteem was positively associated with testing (aOR = 1.06; 95% CI = 1.00-1.12; p = 0.038). Associations with HIV testing behaviour were not significant for self-efficacy, fatalism, gender equity, or sensation seeking. Public health interventions aiming to reduce anticipated stigma and increase self-esteem may potentially increase the uptake of HIV testing among truck drivers. Further research is needed to better understand the influence of these psychosocial characteristics on HIV testing.