The maintenance of assets of an organization within an environment that facilitates employee safety is essential to its growth. However, there is a dearth of detailed knowledge on how maintenance culture and its challenges influence employee safety. Thus, this treatise’s foci were to examine the direct influences of both maintenance culture and its challenges on employee safety and examine the mediating role of the challenges on the path between maintenance culture and employee safety. A positivist explorative research approach was adopted for this study, and data were collected from staff within a specific firm’s maintenance unit. A 5-point Likert scale closed-ended questionnaire was used for the survey. The data garnered were evaluated with partial least squares structural equation modelling (PLS-SEM) of regression analysis. The findings revealed that maintenance culture had a statistically significant influence on employee safety. Furthermore, it was found that challenges of maintenance culture had a statistically significant effect on employee safety. The study also found that there was a complementary partial mediation of the challenges of maintenance culture between the path of maintenance culture and employee safety. The findings of the study could be used primarily within the context of the transport maintenance industry. However, the verdicts of the study may also be generalized for usage in other fields, as it adds on to literature. It is projected that the yields of this study would inform strategic resolutions on maintenance culture by firms to create and maintain impressive levels of employee safety.