Prewriting is the process of generating and organizing ideas before drafting a document. Although often overlooked by novice writers and writing tool developers, prewriting is a critical process that improves the quality of a final document. To better understand current prewriting practices, we first conducted interviews with writing learners and experts. Based on the learners’ needs and experts’ recommendations, we then designed and developed InkPlanner, a novel pen and touch visualization tool that allows writers to utilize visual diagramming for ideation during prewriting. InkPlanner further allows writers to sort their ideas into a logical and sequential narrative by using a novel widget— NarrativeLine. Using a NarrativeLine, InkPlanner can automatically generate a document outline to guide later drafting exercises. Inkplanner is powered by machine-generated semantic and structural suggestions that are curated from various texts. To qualitatively review the tool and understand how writers use InkPlanner for prewriting, two writing experts were interviewed and a user study was conducted with university students. The results demonstrated that InkPlanner encouraged writers to generate more diverse ideas and also enabled them to think more strategically about how to organize their ideas for later drafting.