Most critical literature on online writing tutoring is based on the premise that face-to-face tutorials are—and should be—the preferred method for tutoring academic writing. According to this premise, the pedagogic validity of any other mode of tutoring depends on how accurately it replicates the “ideal” conditions of face-to-face interaction. Following this logic, the asynchronous writing tutorial comes last in the hierarchy of preferred tutorial formats. This chapter offers a different perspective on asynchronous online writing tutoring based on the teaching practices in place at the Centre for Academic Writing (CAW), Coventry University, England. It develops a new theoretical framework for existing tutorial practices and suggests juxtaposition through parenthetical comments as a pedagogically-sound strategy for teaching critical thinking in asynchronous online student-tutor communication and potentially in other teaching contexts. Our analysis relies on Bakhtin’s understanding of language as intrinsically dialogic and applies this concept to the academic discourse of asynchronous writing tutorials.