Research on writing and transfer has shown that writers who have sophisticated rhetorical knowledge are well equipped to adapt to new situations, yet less attention has been paid to how a writer's adaptability is influenced by their writing processes. Drawing on Zimmerman's sociocognitive theory of self-regulation, this study compared the writing processes taken up by graduate student writers composing a research proposal for their final project in a tutor-training practicum. Findings from process logs, interviews, and drafts differentiated self-regulation strategies associated with varying degrees of success. The more successful writers framed problems in terms of potential solutions, used problems to set goals, and reacted to problems by creating a narrative of progress; in contrast, less successful writers avoided problems or framed them as dead-ends. Compared to the less successful writers, the more successful writers concluded the project with robust knowledge about research proposal writing. These findings suggest that self-regulation strategies may be linked to an ability to develop rhetorical knowledge and practices in the face of challenging writing situations.