This qualitative exploratory case study focused on a Professional Development (PD) program for mathematics teachers in the public system, which is an underserved community of teachers in Chile. The study aimed to understand how the program addressed the challenges brought by the pandemic. Using semi-structured interviews and drawing from a pedagogy of connection, this study analysed data from nine participants, who were facilitators and coordinators of the PD program. The findings showed that participants identified three sources of challenges: personal, professional, and operational and that they presented the strategies used for addressing them. The strategies, in general, involved a better understanding of the contexts and teachers they served even though doing so prevented them from meeting some curricular goals. Their strategies highlighted the notions of flexibility, humanising aspects of communication, and innovation to overcome the limitation of using technology in pedagogical contexts.