Expected positive outcomes of teacher supervision in Guyana are not always achieved. This qualitative study explores forces that may be hindering desirable outcomes of supervision provided by Nursery Field Officers (NFOs) and is intended to be an attempt to improve practice. Through thematic analysis of interviews with 30 teachers, five critical areas of undesirable encounters were discovered. These encounters were framed as fault-finding, controlling and mechanically oriented, unproductive, emotionally unsettling, and disruptive. Caution about the danger of identification of pedagogical weaknesses in the absence of accompanying solutions and recommendations is flagged, and remedial strategies are identified. The findings reframe, reinforce, and complement existing knowledge about educational supervision, serve to chronicle Guyanese teachers' experiences with the supervision of NFOs, and might be informative to professional development programs that rely on supervision to sustain pedagogical growth. Program providers and other stakeholders might find the teachers' experiences a reference point to consider critical issues regarding the quality of and approach to supervision.