Provision of healthcare within short-term custody settings such as police watch-houses presents a complex public health challenge. This area has received limited attention in the literature, particularly the viewpoints of paramedics, who are a key link in the chain of healthcare. This study aimed to describe paramedics’ decision-making practices and procedures regarding the transport of patients from the watch-house to the emergency department. A qualitative descriptive study was undertaken utilizing semi-structured interviews with paramedics in Queensland, Australia. A full thematic analysis was not completed due to the small sample and limited data sufficiency. However, interview data were grouped into similar categories with the goal of reporting these novel findings. Six paramedics from five metropolitan, regional, and rural/remote regions participated. Interviews were analysed into four main categories: paramedic’s role, challenges, enablers, and suggestions. Paramedics described their role as being autonomous with decision-making, especially regarding transport to hospital. Reported challenges revolved around the complexity of the patient, environment, and competing health/security needs. A key issue identified by paramedics was perceived dissatisfaction from police when their assessment resulted in a recommendation to transport the patient to hospital. Enablers included the controlled environment of the watch-house and access to watch-house embedded healthcare providers. Suggestions related to improving structures (e.g. paperwork, education, hours of on-site healthcare providers) and processes (e.g. communication, transport). This study provides a unique perspective on the key role that paramedics have in the delivery of the healthcare to patients in short-term custody and accords with findings from previous studies with emergency doctors.