This document describes an "Agony Aunts" workshop activity carried out by PGCE students at Sheffield Hallam University to explore problems related to using digital technologies in educational settings. The activity involved a panel of three students fielding questions from an audience of students about their worst-case scenarios and technology issues. Intended outcomes were to encourage discussion and sharing of best practices in a supportive environment. When implemented, examples of problems discussed included equipment failures and engaging different types of learners with technology. The panel provided solutions and emphasized preparation, alternative plans, and viewing problems as learning opportunities. Overall, the activity helped students share real experiences and practices.