This chapter presents benefits and drawbacks of using humor in learning contexts, including teaching and training. The two main theories about humor and learning, namely the Instructional Humor Processing Theory and the Perceived Humor Hypothesis, are introduced. Among the consequences of humor in instruction are cognitive, social as well as motivational and affective ones: Humor may enhance learning if tied to the course content, humor may increase teachers’ immediacy and the presenter’s likability, and humor may foster positive affect and thus motivation. However, it may reduce the perceived credibility of the presenter and does not necessarily improve effectiveness or performance. Additionally, social aspects such as interpersonal trust may moderate the effects of humor, for instance. Benefits of humor may depend on the mode of presentation, that is, whether humor is used in textbooks, tests, or online instruction. Humor trainings seem to foster knowledge about and usage of humor. Research in school/university settings serves as the basis. Only a few studies focus on instruction and learning in the work context, mainly with regard to creativity as outcome. Future research avenues as well as recommendations for practical use close this chapter. For instance, techniques recommended for teaching students can be applied to trainings or instruction in the work context.