Special education teachers leave the field at a rate that outpaces their general education teacher counterparts, with special education teaching positions unfilled at a rate 5.5 times greater than general education positions (Boe, 2006). This study identified perceptions of risk and resilience in nine first year special education teachers in order to identify how to best support and retain them. Through semi-structured interviews the teachers described their experiences in the following roles (1) co-teaching, (2) self-contained, (3) case management, and (4) "other" (e.g., coach, tutor). Participants identified and positively or negatively ranked six "feeling" words they experienced in each role, which resulted in a portrait of risk and resilience. Results indicated that participants felt the most positive in an "other" and self-contained teaching role with less positive feelings in co-teaching and case management roles. When participants felt supported and perceived that they were making a difference, they felt the most resilient. When participants felt isolated and underprepared, they felt the least resilient. Implications for school-based supports and teacher preparation are discussed.