Automated contextual information retrieval techniques are provided based on multi-tiered user modeling and a dynamic retrieval strategy. Content relevant to a current message is presented by initially obtaining a multi-tiered user model containing a multi-tiered representation of interactions of a first user with each contact, wherein the multi-tiered representation includes a plurality of topic models each corresponding to interactions between the first user and one contact. The topic models contain a set of topics, each containing topic keywords. Context information is extracted based on content of the current message, a sender and/or a recipient of the current message, and the multi-tiered user model. A retrieval strategy is determined based on the extracted context information. Contextual queries are generated to search the information repositories selected based on the determined retrieval strategy. Content relevant to the current message is presented based on search results from the selected information repositories.