This multiple case study explores how three online, high school teachers used technological tools to create meaningful learning activities for their students. Findings reveal that teachers use a wide variety of tools and approaches to online learning. Tools are categorized as content, communication, and management tools. Approaches include utilizing a course management system, a teacher developed and designed course, and Project Foundry, an online management tool for project-based learning. Meaningful learning was observed in all sites. However, key findings reveal that students all had few instances of peer-to-peer collaborative learning, competing issues may replace content area learning in online courses, and available tools are not fully utilized for meaningful learning. (Contains 3 tables and 3 figures.)