In this chapter, the authors consider the use of digital storytelling as a tool for boundary crossing. Media, as an extension of self, has potential to help cross-cultural learning that benefits all stakeholders, but specifically, immigrants and English Language Learners, who often experience school literacy challenges. The authors used Cultural Historical Activity Theory (CHAT) as a lens to view two teacher case self-studies, one in Canada and one in the U.S.A., and to examine how their use of digital storytelling helped elementary ELL students to learn the language of school as well as transfer their knowledge to other students and educators. The findings indicated the importance of creating avenues through which immigrant English learners can develop interpersonal communication skills critical to being successful across cultures. Through an analysis of the cases, the authors present language learning implications for educators.