Engagement and academic success in middle school is critically important to ensure students with disabilities complete high school and have a viable path to and through postsecondary education. Although most middle school students say they want to pursue postsecondary education or training, a significant proportion are not actively engaged in college and career readiness (CCR) activities in middle school. This transition in practice article highlights the importance of early CCR instruction for middle school youth with and without disabilities. Lessons learned from developing an online CCR curriculum and implementing it with middle school youth in inclusive middle school settings will be shared. Access to and comfort with technology, the need for age-appropriate content, and strategies for universally designed curriculum will be addressed. Recommended practices and available resources will be offered to expand educator focus on CCR with middle school youth with a wide range of disabilities.