We investigated emotional design features that may influence multimedia learning with a self-generated learning (SGL) activity, namely answering elaborative interrogations. We assumed that a positive emotional design would be associated with a higher motivation to accomplish the additional SGL activity. Moreover, an interaction was expected: Learners learning with a positive emotional design should profit from learning with elaborative interrogations whereas learners learning with a negative emotional design would not profit from this strategy to the same extent but would rather benefit through reading. Since no negative emotional design existed yet, we additionally took the challenge to construct one. In a preliminary study, the emotional design features were pre-tested for their influence on emotional state and according to evaluation results, emotional design features were modified for the final versions. For the main study, German students (N = 228) were randomly assigned to one of six conditions that resulted from a 3 × 2 Design with emotional design (intended-positive vs. intended-neutral vs. intended-negative) and SGL activity (elaborative interrogations vs. no elaborative interrogations). Contrary to expectations, the intended-negative design worked not out as intended, but was rather comparable with the positive emotional design with respect to learners’ emotional states. Learner motivation was higher when learning with the intended-negative emotional than the neutral design. The quality of the elaborated answers and learner motivation correlated positively with the performance of all learning outcome scores. For transfer questions which addressed the elaborated concepts, an interaction can be reported: learners learning with the positive emotional design benefitted from learning by reading compared to answering the elaborative interrogations. Regarding transfer questions whose concepts were explicitly described in the instructional material, it was better to learn with the intended-negative emotional than the neutral design. According to results of mediation analyses, the influence of motivation on learning outcomes could mostly be explained by the influence of motivation on answering the elaborative interrogations. Implications for creating emotional design as well as its effect on learning are discussed.