Graduates of health-related associate degree programs in Australia require vocational competencies to address real-world issues as a responsible citizen, which aligns with deep learning for 21st century ideals. The research, conducted in a university setting, employed qualitative and quantitative methods, in a bounded case study. Associate degree in health science students’ engagement in learning was explored using two different questionnaire instruments, focus group interview, and for a sub-cohort of participants, undertaking a health promotion and public health elective stream, collaborative experiential learning for entry-level support roles in health was observed via focus group interview, five individual interviews, and student written reflections from 11 participants. Descriptive analysis of quantitative and qualitative data supported an emergent theme that while the associate degree contributed to acknowledged real-life skill development, some limitations in health support role work-readiness was expressed by participants. The case study research indicates that participants showed commitment to pursuing a future health professional career, with the associate degree as their pathway. The findings apply to stakeholders, such as universities offering health-related vocationally oriented associate degree programs to bolster the applied skill content, thus preparing work-ready graduates, which may ultimately benefit the wider health services community.