The purpose of this study was to investigate what was happening in a prematurely terminated supervision case with the focus of observation on the interactions between the supervisor and the supervisee. We analyzed four sessions of one supervisory dyad in order to draw a comprehensive picture of the supervisory process. Our analysis showed that the dropout of this supervisee was caused by a series of mild and severe conflict events. Similar conflicts occurred repeatedly. We found that with the accumulation of unsolved supervision relationship problems, negative emotions of the supervisee grew. Seven poor supervisory behaviors persistently appeared in the supervision. Of these, three were most prevalent: the supervisor confronted and evaluated negatively the supervisee; the supervisor misunderstood the supervisee’s intentions and behaviors, and the supervisor did not focus on the supervisee’s problems or difficulties throughout the supervisory process. We speculated that dropout could have been avoided had the supervisor recognized the factors sabotaging the supervisory relationship and adjusted her interaction styles in relating with the supervisee.