Communication access is a legislated right for deaf people in many settings in the United States; however, the number of professional signed language interpreters does not meet the demand for services (NCIEC, 2009b; NIEC, 2015). One factor of the demand-supply imbalance may be attributed to the number of individuals who exit the interpreting profession at an early stage in their career while still novice interpreters. Using the theoretical framework of attraction, selection, and attrition (ASA) from applied and organizational psychology (Schneider, 1987), along with person-organization fit (PO Fit) as described by Caplan (2011), I examined attrition of individuals from early professional interpreting practice. I surmised that throughout the cycle of ASA, individuals and the profession are continuously examining dimensions of PO Fit and, for some, disruptions arise in the conceptualization of fit. The results of this multiple case study will increase understanding of attrition in the signed language interpreting profession and may lead to a set of strategies to help individuals assess their fit with the profession. Further, the findings may assist the members of the interpreting profession to develop ways to address issues of fit when barriers arise. Critically, retention of signed language interpreters may result in a greater number of available practitioners to provide communication access for the deaf community.