Although prior research, documents, and teachers’ experiences have focused on differentiating a single or a sequence of lessons, the study reported here examined teachers’ attempts to differentiate every class, every day, over an entire semester. The study focused on the ideas of differentiation presented by Tomlinson to examine how mathematics teachers and math intervention specialists address differentiated instruction in remote learning environments. The study coordinated the documentational approach to didactics and Thompson and Harel’s theory of meanings to examine teachers’ (schemes of) meanings as they engaged in and discussed their attempts to differentiate instruction in remote learning environments. Analyses involved teachers’ Reflective Mappings of Resource System and remote interviews. The findings reported here focus on the case of one mathematics teacher and highlight the importance of teachers’ understandings and meanings in their attempts to differentiate instruction and the role digital resources play in supporting or hindering such practices.