This presentation examines learners' understanding and development of difficult spatial prepositional usages of “at,” “from,” “in,” “on,” and “to.” Results indicate semantic complexity and metacognitive understanding of these prepositions are some of the main obstacles for learners to overcome in order to enhance their learning. This ongoing investigation illustrates that a usage-based approach to the development of learning tasks provides an effective strategy to support learners' language development, confidence, and self-efficacy.