This paper explores a Master of Social Work (MSW) student's experiences in engagement with structural social work during an advanced practicum with a perinatal mental health project in Northeastern Ontario. The goals of the advanced practicum were to: (a) improve reflexive practice, (b) improve understanding of structural social work, specific to social justice, and (c) improve understanding of the role of structural social workers within inter-organizational collaborations. Deconstruction of the engagement with each of the goals and the challenges in facilitation of the objectives are reviewed. Though there are issues and dilemmas facing those who wish to engage in structural social work, this advanced practicum experience was successful in improving the student's engagement with structural social work praxis.