In this theoretical essay, I build on complexity theory and commognition to theorize the ways in which failure to teach/learn mathematics (FTLM) emerges through the dynamic interactions among teacher, learner, and curriculum demands. I focus on two main concepts of complexity theory: emergence in dynamic systems and attractor states (stable, self-reinforcing patterns), and link them to the commognitive terms of ritualization (rigid focus on procedures and lack of agency) and identity. The complexity-commognitive view of FTLM is first contrasted against common, more linear explanations of FTLM. This view is then illustrated with two case studies--one exemplifying in micro-scale the short-term stabilization of ritualization in the interactions between the author and Dana, a 7th grade student identified as failing persistently in mathematics; the second exemplifying the temporal emergence of ritualization as an attractor state across 2 years (grades 7-9) in the case of a student, Idit, who was originally identified as a strong student and over the years developed an identity of failure. Finally, I discuss methodological, empirical, and practical implications of this complexity-commognitive view of FTLM.