Many web search improvements have been developed since the advent of the modern search engine, but one underrepresented area is the application of specific customizations to search results for educational web sites. In order to address this issue and improve the relevance of search results in automated learning environments, this work has integrated context-aware search principles with applications of preference based re-ranking and query modifications. This research investigates several aspects of context-aware search principles, specifically context-sensitive and preference based re-ranking of results which take user inputs as to their preferred content, and combines this with search query modifications which automatically search for a variety of modified terms based on the given search query, integrating these results into the overall re-ranking for the context. The result of this work is a novel web search algorithm which could be applied to any online learning environment attempting to collect relevant resources for learning about a given topic. The algorithm has been evaluated through user studies comparing traditional search results to the context-aware results returned through the algorithm for a given topic. These studies explore how this integration of methods could provide improved relevance in the search results returned when compared against other modern search engines.