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The COVID-19 pandemic and the requirement for social distancing led to the closure of extracurricular activities that usually involve teamwork and collaboration, such as math clubs. Research on the design and effectiveness of extracurricular mathematical activities that aim to promote student interest and improve mathematical skills is limited, particularly in these challenging times. This exploratory case study examines an online after-school program, the Tecn@Mat Club, aimed at promoting middle grade students’ ability in solving mathematical problems with digital technologies during the pandemic. Based on document analysis, observation of the club sessions, questionnaires, and interviews with the participants (students and a mathematics education expert), this research documents the design and implementation of the Tecn@Mat Club, as well as its participants’ experiences and perspectives regarding the activity in which they engaged. The main results show the feasibility of adapting in-person, after-school math activities for an online setting, engaging middle grade students in mathematical problem-solving with technology by providing moderate mathematical challenges and promoting collaborative work. Results of a SWOT analysis (the acronym for strengths, weaknesses, opportunities, threats) allow for the identification of the key features to preserve and challenges to overcome in future replications of the club. Limitations of this study and future research directions are discussed.