Web search is increasingly used to satisfy complex, exploratory information goals. Exploring and synthesizing information into knowledge can be slow and cognitively demanding due to a disconnect between search tools and sense-making workspaces. Our work explores how we might integrate contextual query suggestions within a person’s sensemaking environment. We developed InterWeave a prototype that leverages a human wizard to generate contextual search guidance and to place the suggestions within the emergent structure of a searchers’ notes. To investigate how weaving suggestions into the sensemaking workspace affects a user’s search and sensemaking behavior, we ran a between-subjects study (n=34) where we compare InterWeave’s in context placement with a conventional list of query suggestions. InterWeave’s approach not only promoted active searching, information gathering and knowledge discovery, but also helped participants keep track of new suggestions and connect newly discovered information to existing knowledge, in comparison to presenting suggestions as a separate list. These results point to directions for future work to interweave contextual and natural search guidance into everyday work.