Although increasingly encouraged to incorporate digital media into classrooms to prepare students for engaged participation in a digital world, teachers are often taken by surprise when paradigm clashes arise between traditional school expectations and the affordances of these new spaces. Through data gathered from ethnographic methodologies during a rich teacher-researcher partnership, this research foregrounds tangles that emerged when a high school English teacher and a partnering researcher adopted new media tools and pedagogies in two traditional English classes. They concluded that each tangle found its genesis in two competing urges teachers experience when engaging in pedagogical design: the desire to maintain traditional English class norms and the desire to reshape and reimagine it. This collision of strategies and tactics emerged in five distinct categories: vantage points, genres, boundaries, tasks, and expectations. These results indicate a need for greater awareness of the difficulties in the maintenance of new classroom spaces; attention to the complex negotiations required when teachers juggle technological knowledge, pedagogical knowledge, and content knowledge; and the need for teacher education to create more space for future teachers to work with these tensions through reflection upon collaborative pedagogical design practices in authentic classroom environments.