Mandated policies to improve food environments in public settings are an important strategy for governments. Most Australian governments have mandated policies or voluntary standards for healthy food procurement in healthcare facilities, however, implementation and compliance are poor. A better understanding of the support required to successfully implement such policies is needed. This research explored food retailers’ experiences in implementing a mandated food and nutrition policy (the Policy) in healthcare settings to identify barriers, enablers, and impacts of compliance. Three 90-min workshops facilitated by two public health practitioners were undertaken with 12 food retailers responsible for operating 44 outlets across four hospitals in Perth, Western Australia. Workshop discussions were transcribed non-verbatim and inductive thematic content was analyzed. Three main themes were identified: (1) food retailers had come to accept their role in implementing the Policy; (2) the Policy made it difficult for food retailers to operate successfully, and; (3) food retailers needed help and support to implement the Policy. Findings indicate the cost of implementation is borne by food retailers. Communications campaigns, centralized databases of classified products, reporting frameworks, recognition of achievements, and dedicated technical expertise would support achieving policy compliance. Feasibility assessments prior to policy implementation are recommended for policy success.