In this chapter we discuss how applying the concept of finding “trouble” to our teaching provides a bridge between first-year writing and rhetorical analysis assignments and primary source literacy skills that can be adapted for use in many types of primary source sessions across disciplines. The concept of “trouble” in this context is defined as any element of an archival source item—whether it be the text, language, narrative, structure, format, or materiality—that is unfamiliar, challenges common knowledge or assumptions, flips a common narrative, reveals something unexpected, or presents an alternative point of view.