In this paper we examine data from a complex two-day experiment with professional cyber red teamers to determine what creates, or contributes, to affective states that may further disrupt attackers. Participants rated their frustration, surprise, confidence, self-doubt, and confusion at the end of each day, and these responses were scored on a Likert scale and using Thematic analysis. We found several elements strongly contributed to the frequency and severity of these affective states, supporting our initial hypothesis, and further that (1) experiencing a Lack of Progress impacted four of the five states with moderate severity, and (2) interacting with elements in the environment that Deviated from what was expected was associated strongly with surprise. Implications for cyber defense and limitations of the method are discussed. © 2023 Human Factors and Ergonomics Society.