When learning new vocabulary, both humans and machines acquire critical information about the meaning of an unfamiliar word through contextual information in a sentence or passage. However, not all contexts are equally helpful for learning an unfamiliar ‘target’ word. Some contexts provide a rich set of semantic clues to the target word’s meaning, while others are less supportive. We explore the task of finding educationally supportive contexts with respect to a given target word for vocabulary learning scenarios, particularly for improving student literacy skills. Because of their inherent context-based nature, attention-based deep learning methods provide an ideal starting point. We evaluate attention-based approaches for predicting the amount of educational support from contexts, ranging from a simple custom model using pre-trained embeddings with an additional attention layer, to a commercial Large Language Model (LLM). Using an existing major benchmark dataset for educational context support prediction, we found that a sophisticated but generic LLM had poor performance, while a simpler model using a custom attention-based approach achieved the best-known performance to date on this dataset.