Abstract-This study, based on a case study research design, aimed to identify Taiwanese elementary students' difficulties in the process of generating multiple-choice items in the subject of social studies. Six sixth grade pupils with different achievement levels were recruited to participate for the entire 2015 school year. Each participant was required to pose two multiple-choice items in 20 minutes in class after the teacher finished teaching each social studies unit (24 units in total). Data collection methods included participant observations, document analysis of student-generated questions, and individual face-to-face interviews. The qualitative data analysis method was adopted for inducing convergent themes. Four main themes emerged related to the difficulties in student question-generation: finding appropriate content and the main ideas of the study material to construct questions on, completing the specified number of questions with options of adequate quality, formulating linguistically appropriate question stems, and constructing questions that involve higher-order cognitive levels. Based on the findings obtained from this study, explicit pedagogical suggestions regarding supports to help mitigate the difficulties that students encountered during student question-generation are provided, with their applicability to other larger contexts attended to.