In this study, 11 Swedish occupational safety and health (OSH) inspectors were interviewed about their views of and experiences interacting with micro-enterprises (1-9 employees). The qualitative content analysis found one theme, “Falling outside the system”, and three subthemes, “The inspector—shaped by specific standards”, “The bureaucrat and the micro-entrepreneur—two separate worlds”, and “System faults and system changes”. According to the inspectors, the Swedish OSH regulatory system, with inspectors on the front line, neglects the specific needs, circumstances and characteristics of micro-enterprises. Therefore, we suggest revising the OSH regulatory system and following inspection methods and enforcement styles to better address the needs of micro-enterprises.