This chapter explores the dilemmas that we, two Australian researchers, faced as we worked with school communities to improve students’ literacy outcomes. Our current research focuses on literacy learning and teachers engaging parents, community members, and students in curriculum inquiry, which integrates social media use. Combining a design-based research approach and social media channels, we research amidst the fray of emerging and sometimes changing policy mandates, political and cultural change in school systems, and rapidly developing digital technologies. This chapter uses the research method of metalogue as a reflexive approach to render visible the methodological and ethical dilemmas in our current research. In presenting our metalogue, we explain not only how we brokered our way through the dilemmas that arose but also how we created opportunities for innovative classroom practice and thus literacy research. We draw conclusions from our experience about the importance of doing difficult research and offer hope to future researchers who, like us, approach their work with bold plans to improve literacy education for all students.