The purpose of this research was to investigate the effects of using cognitive and metacognitive prompting strategies in a web-based learning environment to engage college students in a complex, ill-structured task. The course context was a freshman/sophomore level Information Sciences and Technology course, and the topic was web design. Four ill-structured problem-solving outcomes were measured: problem representation, developing solutions, making justifications, and monitoring and evaluation. Findings showed significant effects of the prompting treatment on all four ill-structured problem solving outcomes. (Contains 5 tables and 1 figure.)