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Recent research indicates that Web 2.0 applications contribute to supporting a social constructivist approach for language learning. However, students encounter different types of barrier associated with technologies and learning tasks, which can cause disengagement during different phases of learning. Thus, based on flow theory and the strategic motivation framework, this study aims to investigate students’ motivation and their engagement patterns while participating in Web 2.0 digital storytelling activities. The participants are 24 elementary school students of a suburban school in northern Taiwan. Over 19 weeks of observations on students aged 9–10 years in a third-grade classroom, data were collected through three sources: surveys, students’ digital stories, and English tests. The analysis of the data showed that motivation was a dynamic process, initially low but increasing in later phases. A dynamic pattern was also identified in the students’ flow perceptions, which included two cycles of disengagement and reengagement. Students encountered different challenges that led to disengagement phases, which highlighted the need for specific types of learning support in elementary school contexts. In addition, the participants’ vocabulary and oral fluency were found to have been enhanced by the end of the study. The implications for educational practice are discussed and the direction for future studies addressed.

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