This conceptual article makes the argument that the fields of English language arts and composition studies require a more robustly elaborated theoretical perspective on the identity development of preservice teachers as teachers of writing due to the rapid proliferation of AI-assisted technologies in learning spaces. Thus, the authors utilized the conceptual frames of activity theory and dilemmatic spaces to consider how personal epistemologies and dimensions of writing theory interrelate to inform the ways teachers of writing construct and conceptualize their writing pedagogies related to AI chatbot platforms and AI-assisted applications. By including dilemmatic space as a component within a teacher's construction of self as teacher of writing, the authors highlight their belief that in a landscape cluttered with generative AI aimed at and sold to teachers as measures of efficiency and consistency, the dilemma to use or not to use is no longer a singular event. Instead, the concept of dilemmatic space provisions the opportunity to consider the dynamic spatial, interpersonal, and intrapersonal conditions that shape the positions individuals take toward themselves, others, and the tools they use in day-to-day learning and teaching interactions. Teacher educators should forward technocritical inquiry opportunities and conversations with preservice teachers, such that they all develop technoskeptical dispositions toward AI platform technologies and writing instruction. Ideally, decisions to integrate AI platforms into writing instruction will become increasingly thoughtful, intentional, well-reasoned, and student-centered rather than driven by presentist concerns to maximize productivity.