General labor market condition is an important contextual factor influencing employment opportunities and outcomes for people with disabilities and is particularly significant given the recent economic recession. Yet, longstanding data analytic strategies have focused only on individual predictors rather than the dynamic interaction among individual level and organizational/environmental level variables, such as considering the role of labor market conditions. This study used the Rehabilitation Services Administration Case Service Report (RSA-911) data for fiscal years 2005 and 2009 to represent two distinct time periods, one before and one during the U.S. economic recession, respectively. Hierarchical linear modeling was used to examine the relationship between state unemployment rate and its interaction with personal factors influencing the employment outcomes of people with disabilities receiving state vocational rehabilitation services. Results found negligible between-state differences, but state unemployment rates were found to moderate the relationships between some demographic variables and successful competitive employment vocational rehabilitation (VR) case closure. Specifically, the significance and magnitude of those effect sizes varied by general economic context. These findings call attention for the need to consider the role of contextual variables, such as state unemployment rates, and their impact on the predictive strength of specific demographic and disability variables on employment outcomes for people with disabilities.