The need for representative samples in research is well-accepted and widely acknowledged. However, marginalized populations experiencing poverty, including unstably housed youth and youth experiencing homelessness, are consistently underrepresented. This underrepresentation has implications for fully understanding and addressing the needs of youth lacking adequate shelter and reduces the quality of the information available to inform intervention design and systems change. In particular, rigorous and representative youth engagement in research is essential in the design of robust prevention strategies at intervention and policy levels. The current paper summarizes lessons learned from three leading research teams in the field of youth homelessness, located in Canada and the United States, in the form of a framework for successful research engagement of youth with experiences of homelessness. Collaborative discussion with researchers and youth with lived experience generated an expert consensus of strategies crucial for successful research engagement. This consensus was summarized with five pillars of successful engagement that were relevant across settings: attunement, accessibility, communication, collaboration, and flexibility. The authors also highlight notable challenges and future directions. The objective of this paper is to introduce guiding principles that will both motivate and inform researchers undertaking research efforts with unstably housed youth, and to initiate further discussions on adapting engagement methods to meet the needs of marginalized youth populations.