Objective: Men who experience homelessness in Australia often have complex health and social issues, including the trimorbidity of concurrent mental illness, substance use disorders and physical health conditions. These men tend to have poor health outcomes, and present challenges to healthcare systems. To improve system responsiveness and patient outcomes, the perspectives of marginalised groups need to be understood. Methods: Five focus groups were conducted with 20 men in a homeless men's hostel, exploring their experiences of seeking and receiving health care, and views about improving these. An inductive thematic analysis was undertaken. Results: Several participants expressed gratitude for care provided for life-threatening physical illness and trauma. However, negative experiences of health system responses were more frequently reported. Four emerging themes all made securing effective 'tickets of entry' to health care more difficult: dismissive care, care fragmentation, inconsistent medical management of pain and inadequate acknowledgement of psychological distress. Conclusions: Improvements are needed in care integration and the de-escalation of potentially confrontational interactions. Effective, safe and compassionate system responses to presentations of psychological distress and pain should be collaboratively developed. Some current responses may entrench stigma, further traumatising vulnerable patients. What is known about the topic?: Men who experience homelessness have poor health outcomes and present challenges to healthcare systems. What does this paper add?: This paper describes healthcare experiences and insights of men who are experiencing homelessness in Australia. These men reported experiencing dismissive care, care fragmentation, inconsistent, inadequate and/or unsafe prescribing for pain and inconsistent and/or ineffective responses to psychological distress. What are the implications for practitioners?: Changes are needed in health system responses, informed by the experiences and insights of marginalised people, to break cycles of trauma and exclusion.