We describe a modern deep learning system that automatically identifies informative contextual examples (\qu{contexts}) for first language vocabulary instruction for high school student. Our paper compares three modeling approaches: (i) an unsupervised similarity-based strategy using MPNet's uniformly contextualized embeddings, (ii) a supervised framework built on instruction-aware, fine-tuned Qwen3 embeddings with a nonlinear regression head and (iii) model (ii) plus handcrafted context features. We introduce a novel metric called the Retention Competency Curve to visualize trade-offs between the discarded proportion of good contexts and the \qu{good-to-bad} contexts ratio providing a compact, unified lens on model performance. Model (iii) delivers the most dramatic gains with performance of a good-to-bad ratio of 440 all while only throwing out 70\% of the good contexts. In summary, we demonstrate that a modern embedding model on neural network architecture, when guided by human supervision, results in a low-cost large supply of near-perfect contexts for teaching vocabulary for a variety of target words.