We study how conditioning context shapes personalization behavior in a teacher-facing educational recommender system. We compare contextual conditioning based on the current student question with memory-based conditioning using persistent learner information. Using deviation correlation and paired statistical tests, we find that contextual recommendations exhibit stronger question-level responsiveness, while memory-based recommendations exhibit history-dependent behaviors, including learner-specific differentiation under identical input. Teacher-facing evaluation signals suggest these recommendations are interpretable and actionable. These results indicate that embedding-based similarity metrics capture responsiveness to the current question but do not characterize personalization grounded in learner history, motivating behavior-level diagnostics for studying conditioning effects.