This paper seeks to gain an insight into counselling supervision experiences of Singapore school counsellors (SCs). In-depth, semi-structured interview sessions with 14 SCs were conducted. Their taped interviews were transcribed and analysed using Interpretative Phenomenological Analysis (IPA). Positive and negative aspects of their experiences included feeling more connected with other counsellors, experiencing a safe environment for sharing, and having supervision as a source of support and help; and feeling nervous about being judged or assessed, lacking in structure, and not having enough time in supervision. The Integrated Developmental Model (IDM) and Discrimination Model (DM) are discussed here to provide a framework for understanding the experiences of the SCs in group supervision.