Writers often address letters to people with whom they have few if any personal connections. To increase understanding of rhetorical decision making in such noninterpersonal settings, this article analyzes letters to a United States senator. The analysis draws from three bodies of research on persuasion: situational context, persuade package, and personal constructs. On the basis of that theoretical grounding—and using deliberative democracy theory and the strategic-choice model—the authors develop hypotheses linking situation attributes and writer attributes to letter attributes. The results show that topic, position, sex, and technology are significantly related to the writer’s choice of appeals, argumentative complexity, and structural directness. They also demonstrate a strong link between technology and message length. These results raise several possibilities for further study, such as whether advocates sometimes address messages to an accessible person while aiming their argumentation at an archetypal authority figure.