As preparation for the rhetoric and composition job market becomes more readily available through multiple sources, some cover letter writers may need clarification on the well-meaning but perhaps conflicting responses to writing given to them by mentors from differing backgrounds, statuses, and epistemes. This article seeks to illuminate the rhetorical situation behind the cover letter with simulated writing responses to a genuine cover letter by five reader archetypes: a supportive reader, a critical reader, an outside reader, a teaching-centric reader, and a research-centric reader. Through this exercise, cover letter writers are shown how to weigh writing advice through the juxtaposition of each reader's response. Cover letter readers as a secondary audience are also considered for preparing future job market participants.