The use of personality measures for pre-employment selection continues to be decidedly strong. Nationwide retailers have opted to administer these assessments increasingly via computer for prospective employees ranging from entry-level worker to upper-level manager positions. School-to-Work transition students with mental and physical disabilities are among the individuals completing these assessments. Nonetheless, the validity evidence supporting their use with this population remains unclear. Because school-to-work transition programs are designed to enhance students' work competence and ultimately employability, schools need to not only develop students' technical knowledge, but also prepare students to handle taking the personality assessments. This is explored in this chapter.