Understanding technological literacy for technical communicators is crucial for effective pedagogy in technical and professional communication. Challenges of teaching technical communication students the functions and concepts of workplace software include the number of rapidly changing applications, a desire to focus on education over training, limited faculty expertise in software, limited resources for teaching software, and a desire to focus on technical communication principles. To address these challenges, the authors explore how to use a four-level framework of technological literacy along with existing resources to design a course to help students use, understand, and evaluate technical communication technology.