While the culture of typical Millennial students, those born after 1978–82, is increasingly recognized as being different from previous generations, particularly with regard to how technology is perceived and used, relatively little is known regarding whether these same characteristics are exhibited by students with mild disabilities. This article explores three cultural dimensions of technology-use patterns by Millennial students having particular relevance to students with mild disabilities: (a) comfort with technology, (b) connectivity to the world, and (c) technology as a tool for learning. An argument is presented that current education professionals who must now consider assistive technology (AT) for these students, know little about their preferences for, choices among, and usage of common non-school technologies that may have substantive implications for AT service delivery.