Because traditional schools struggle to effectively understand, implement, and sustain digital learning initiatives, innovating with digital media in classrooms is a difficult endeavor. Practitioners need examples to better understand conditions necessary to move forward with digital media and learning (DML) in schools. This article provides examples and supports research proposing that context and culture matter when innovating in schools. Three classroom cases using Web 2.0, app development, and game design are discussed, offering educators a pathway to consider similar pedagogical and participatory approaches to foster learning. Classroom contexts, teachers' perspectives, district supports, technical requirements, and scalability are highlighted. The examples suggest innovative DML initiatives can flourish within schools when participants are mindful of context and when a participatory culture is supported (Jenkins, Clinton, Purushotma, Robison, & Weigel, 2006).