In line with Vygotsky’s sociocultural theory (SCT) of mind, digital game-based language learning (DGBL) and dynamic assessment (DA) offer language learning opportunities via sociocultural engagement. This quantitative study explored the role of pragmatic learning strategies (PLSs) and gender in game-based group dynamic assessment. Our participants included thirty upper-intermediate EFL learners (15 males and 15 females) from two intact classes taking an English pragmatic course via game-based group dynamic assessment. Following a pre-test, treatment, and post-test design, the participants filled out a PLS inventory to identify the strategies for tackling L2 conversations in different situations. Besides, all learners were required to write reflective journals following each treatment session. Descriptive statistics and correlational analysis were employed to analyze the data. The findings indicated that the participants most widely used memory strategies, i.e., they relied more on memorizing and storing previous pragmatic knowledge. In addition, compensatory strategies were positive but weak predictors of the learners’ L2 pragmatic performance, and gender did not impact the learners’ use of different PLSs. The study’s limitation and its practical and pedagogical implications for educational policymakers, teacher education programs, and L2 instructors will be discussed in light of the posed research questions.