School administrators are often responsible for observing and evaluating special education teachers. The current study examined the training school administrators received, their needed knowledge and supports, and their confidence in performing job functions related to special education teacher evaluation. A total of 929 school administrators in California completed a 26-item survey in which they reported the training they had received, the usefulness of the training for informing practice, and the confidence they felt in evaluating special educators. Results indicated that most school administrators did not have a background in special education, did not receive training related to evaluating special educators, and felt less confident evaluating special educators than general educators. School administrators, especially those without a background in special education, may need more training and support related to evaluating special education teachers during preparation and in the early years of administration. Training and support should focus on evidenced-based practices for teaching students with disabilities.