This chapter introduces the rhetorical situation as the essential starting point for all effective writing, including writing assisted by AI. It describes a practical framework for rhetorical situation analysis that undergraduate writers can use to make key decisions about their communications. The chapter then integrates AI into this framework to help students better understand their audience, clarify their purpose, assess their context, and adapt their work across media and genres. Using prompt libraries, roleplay exercises, and visual tools, the chapter helps undergraduates build rhetorical awareness and apply it to common tasks like resume writing.