In rural areas, transition planning for young adults with disabilities presents considerable challenges, including linkage to employment upon completion of special education services. Two assessment programs, described in this article, work in concert to assist transition teachers and youth with disabilities in rural areas and include: (a) web-based job preference and job matching assessments, and (b) a social network assessment. An internet-based assessment (www.yesjobsearch.com) presents 2-4 min of video for up to 120 entry-level jobs and allows a job seeker to select preferred ones. A job matching assessment determines the extent to which the job seeker's current skill level matches preferred jobs. Once preferred and well-matched jobs are identified, the social network assessment identifies family, friends, acquaintances, and resources associated with the job seeker's most-preferred/best-matched job. The article describes use of these assessments to facilitate job placement for youth with disabilities in rural areas.