Youth work offers dynamic and rewarding experiences for frontline workers; however, the contestation between the prioritization of communal and neoliberal notions of equity create tensions within the youth sector. While youth workers benefit from reciprocal, fulfilling, and transformational elements in their work, which align with their vocation and values, a critical analysis may expose layers of structural violence, including chronic precarity, overwork, moral distress, underappreciation, tokenization, and silencing. These contradictory dynamics can limit the full potential of youth workers’ critical impact, which seeks to support and advocate for social justice on a communal and systemic level in addition to providing interpersonal services. To explore how the social service sector can better optimize policy and practice while reaffirming frontline workers’ ethical principles of equity, this study investigates how youth workers in Central Ontario navigate factors that support and obstruct their critical (anti-oppressive) practices. Grounded in historical and socio-political contexts, this research examines twenty-five semi-structured interviews utilizing Reflexive Thematic Analysis (Braun & Clarke, 2022/2024). Incorporating the concepts of Critical Pedagogy (Freire, 1970/2000) and praxis to examine the supportive factors, and Structural Violence (Galtung, 1969) and apraxis to examine the obstructive factors, this study presents a discursive model which combines theoretical frameworks with lived experience. The findings of this study provide a model that illustrates the dynamic relationship between five principles of critical practice (relational, holistic, responsive, transformational, and reflexive) and twelve supportive and obstructive factors that have a significant impact on critical youth work. By grounding these lived experiences in shared conceptual language to deconstruct dynamics of the “Social Service Industrial Complex,” this dissertation presents implications for critical praxis in research, policy, and practice.