It is well-known that a key to promoting students’ mathematics learning is to provide opportunities for problem solving and reasoning, but also that maintaining such opportunities in student–teacher interaction is challenging for teachers. In particular, teachers need support for identifying students’ specific difficulties, in order to select appropriate feedback that supports students’ mathematically founded reasoning without reducing students’ responsibility for solving the task. The aim of this study was to develop a diagnostic framework that is functional for identifying, characterising, and communicating about the difficulties students encounter when trying to solve a problem and needing help from the teacher to continue the construction of mathematically founded reasoning. We describe how we reached this aim by devising iterations of design experiments, including 285 examples of students’ difficulties from grades 1–12, related to 110 tasks, successively increasing the empirical grounding and theoretical refinement of the framework. The resulting framework includes diagnostic questions, definitions, and indicators for each diagnosis and structures the diagnostic process in two simpler steps with guidelines for difficult cases. The framework therefore has the potential to support teachers both in eliciting evidence about students’ reasoning during problem solving and in interpreting this evidence.