This article delves into the typically unexamined complexities of conducting research with vulnerable populations, specifically focusing on trans and gender-diverse children and youth. While ethical guidelines exist, there are persistent knowledge gaps in genuinely collaborative research practices with vulnerable populations. Using collaborative autoethnographic methodology, the study draws on the narratives and reflexive accounts of four researchers to explore the complexities of oppression. The article argues for the necessity of a coalition of knowledge and multi-positional perspectives to develop sensitive and rigorous intervention strategies and policymaking. We propose the adoption of two theoretical frameworks: intersectionality and queer reflexivity, to guide our reflections and enhance research outcomes. By acknowledging and integrating diverse positionalities, collaborative approaches can increase the sensitivity, relevance and impact of research. The article proposes that recognising the intersectionality and temporality of researchers’ and participants’ identities can help to effectively navigate complex ethical, methodological and empirical research terrain. This we argue, ultimately contributes to more robust knowledge production, inclusive and impactful research outcomes. In conclusion, the study highlights the significance of embracing coalition and multi-positionality in anti-oppressive research endeavours that can provide diversified perspectives and interventions to better address the complex and multifaceted nature of oppression.