Over 600,000 people leave state and federal prisons each year to re-enter society in the United States. Upon reentry, they face an uphill battle to secure a steady source of income through traditional employment, leading many to start their own businesses, sometimes as a last resort. While transactional work is often straightforward (incorporate an LLC, draft a service contract), there are knowledge gaps in providing legal services for justice-impacted individuals. Because this community is often still under some form of state control or vulnerable to recidivism, transactional clinics can benefit from co-counseling with criminal defense clinics or immigrant rights clinics. This concurrent session will explore how clinicians from various disciplines can work together to provide the best legal support to justice impacted entrepreneurs. Conversely, we will explore how criminal defense clinics and immigrant rights clinics can better support self-employed clients. We will describe scenarios in which knowledge of the criminal justice system or the “crimigration” system are useful to planning transactional work. In some situations, knowing these nuances can dramatically change how a transactional student attorney would approach their matter. Additionally, through collaboration with justice system-adjacent clinics, student attorneys can learn different approaches to representation, such as “trauma-informed lawyering” which will help them better meet the emotional needs of justice-involved clients. Criminal defense and immigrant rights student attorneys can learn how to issue spot financial issues that may affect other parts of their client’s representation. We hope to draw participants from transactional clinics, criminal defense clinics and immigrant’s rights clinics. To make sure our session is interactive, we would like to invite participants to brainstorm concrete ways our clinics can collaborate, with particular attention to identifying gaps in our respective representation.