The use of breakout rooms is an increasingly used tool in online teaching. This study uses Laurillard’s (2013) Conversational Framework to evaluate the effectiveness of breakout rooms in achieving learning through peer-to-peer dialogue in large-scale teaching. Data were collected through online surveys, comprising Likert ratings and open questions, to undergraduate students (n = 115) and tutors (n = 9) at Aberdeen Business School (Robert Gordon University) reflecting on Year 1 studies in the 2020–2021 academic year. Key findings indicate that breakout rooms can be successful in achieving effective learning through peer-to-peer dialogue. However, this is highly dependent on the participation by students, which was variable. In order to facilitate effective breakout rooms, tutors need to ensure they set a clear task, with evidence suggesting a perception gap between tutors and students on how effectively this was done, and regularly visit breakout rooms to encourage participation and provide support.