Men generally fare worse than women across the HIV cascade. While we know much about how men perceive the health services, we know little about how health workers (HWs) themselves have experienced engaging with men and what strategies they have used to improve this engagement. We interviewed 12 HWs in public health care services in Cape Town to better understand their experiences and perspectives. Health workers felt there were significant gaps in men's engagement with HIV care and identified masculine gender norms, the persistent impact of HIV stigma, and the competing priorities of employment as key barriers. They also highlighted a number of health service-related challenges, including a poor perception of the patient-provider relationship, frustration at low service quality, and unrealistic expectations of the health services. Health workers also described several strategies for more effectively engaging men and for making the health services both more male friendly and more people friendly.