The goal of the current descriptive and comparative study is to develop a more comprehensive understanding of the employment realities of recent junior/community college and university graduates and premature leavers (i.e., those who drop out before completing their program of study) with disabilities. We investigate the following research questions related to employment: (a) What are the characteristic of individuals who are employed and of individuals who are not employed? (b) Why are unemployed individuals unable to find work? and (c) Why do some individuals stay out of the labour force (i.e., not employed or looking for work: Statistics Canada, 2008a)? We also examine (d) the role of the following in finding employment: grades, highest qualification attained, and type of disability/impairment as well as (e) job satisfaction and its relation to program of study. Between 11% and 14% of current junior/community college and university students have a disability both in Canada (Ministry of Training Colleges and Universities, 2012) and the United States (Snyder & Dillow, 2012). Therefore, understanding the transition of well-educated youth with disabilities from postsecondary studies to employment is of great importance. Understanding this transition is vital given that postsecondary students with disabilities graduate at the same rate as students without disabilities, with the main difference being that they take additional time to do so (Jorgensen, Fichten, Havel, Lamb, James, & Barile, 2005; Wessel, Jones, Markle, & Westfall, 2009).