In this dissertation, I analyze the organizational and political constraints that technical writers encounter when dealing with complex rhetorical situations, particularly within risk-management discourse. I ground my research in case studies of safety briefings that airlines provide to their passengers because these important documents have long been regarded as ineffective, yet they ve gone largely unchanged in the last 20 years. Airlines are required to produce these safety briefings, which must satisfy multiple audiences, such as corporate executives, federal safety inspectors, flight attendants, and passengers. Because space and time are limited when presenting safety information to passengers, the technical writers must negotiate constraints related to issues such as format, budget, audience education and language, passenger perceptions/fears, reproducibility, and corporate image/branding to name a few. The writers have to negotiate these constraints while presenting important (and potentially alarming) information in a way that s as informative, realistic, and tasteful as possible. But such constraints aren t unique to the airline industry. Once they enter the profession, many writing students will experience complex rhetorical situations that constrain their abilities to produce effective documentation; therefore, I am looking at the theories and skills that we re teaching our future technical communicators for coping with such situations. By applying writing-style and visual-cultural analyses to a set of documents, I demonstrate a methodology for analyzing complex rhetorical situations. I conclude by proposing a pedagogy that teachers of technical communication can employ for helping students assess and work within complex rhetorical situations, and I offer suggestions for implementing such practices in the classroom.