Social media sites are where life happens for many of today's young people, so it is important to teach them to use these sites safely and effectively. Many youth receive classroom education on digital literacy topics, but have few chances to build actual skills. Social Media TestDrive, an interactive social media simulation, fills a gap in digital literacy education by combining experiential learning in a realistic and safe social media environment with educator-facilitated classroom lessons. The tool was piloted with 12 educators and over 200 students, and formative evaluation data suggest that TestDrive achieved high levels of engagement with both groups. Students reported the modules enhanced their understanding of digital citizenship issues, and educators noted that students were engaging in meaningful classroom conversations. Finally, we discuss the importance of involving multiple stakeholder groups (e.g., researchers, youth, educators, curriculum developers) in designing educational technology.