Generational differences have been widely discussed; attention to and speculation on the characteristics of the Millennial Generation are especially abundant as they pertain to the use of educational technology for education and training. A careful review of the current popular and academic literature reveals several trends. First, whether based on speculation or research findings, discussion has focused on traits of the newer generations of students and workers and how their needs, interests and learning preferences can be met using new media, innovative instructional design and digital technologies. Second, generally speaking, although in the past few years there have been more critical and diverse perspectives on the characteristics of the Millennial Generation reported in the literature than before, more substantive studies in this area are still necessary. This chapter discusses trends and findings based upon the past 10 years´ literature on generational differences, the Millennial Generation, and studies and speculations regarding school and workplace technology integration that is intended to accommodate generational differences. There is still a lack of consensus on the characteristics of the newer generation sufficient to be used as a solid conceptual framework or as a variable in research studies; thus, research in this area demands an ongoing, rigorous examination. Instead of using speculative assumptions to justify the adoption of popular Web 2.0 tools, serious games and the latest high tech gear to teach the Millennial Generation, approaches to integrating technology in instruction, learning, and performance should be determined by considering the potential pedagogical effectiveness of a technology in relation to specific teaching, learning and work contexts. Clearly, today´s higher education institutions and workplaces have highly diverse student bodies and work forces, and it is as important to consider the needs of older participants in learning with technology as it is to consider those of the younger participants. Recommendations for future research and practices in this area conclude the chapter.