It is widely recognized that people experiencing homelessness are over-criminalized and often deal with negative interactions with police that result in tickets or criminal charges. Therapeutic courts and diversion-focused programs exist and are important, but most people are still left to negotiate difficult court processes with legal aid or pro-bono support. In this presentation, I explore when and how criminal defense lawyers represent people experiencing homelessness – via specialized programs or through the regular court process. I document how they collect and use information about their client’s personal social history at different stages of the judicial process, like at bail and sentencing. Lastly, I analyze how the COVID-19 pandemic has shaped legal representation of people experiencing homelessness. This qualitative study is based on interviews with criminal defence lawyers in two large Canadian cities (N=80), allowing for some comparative analysis. I examine logics, practices and mechanisms that attempt to improve how the justice system can and should adapt to their socio-economic situation. My work contributes to scholarship about institutional revolving doors, the criminalization of homelessness, therapeutic justice, and emerging jurisprudence that recognizes systemic injustice.