Interpretative phenomenological analysis was used to explore the simultaneous supervision experiences of counselors-in-training. Simultaneous supervision is when a supervisee receives clinical supervision from multiple supervisors. Sometimes this supervision includes a university supervisor and a site supervisor. Other times this supervision occurs when a student has multiple sites in one semester and receives supervision at each site. Counselors-in-training described their experiences with simultaneous supervision during the course of their education. Four superordinate themes emerged: making sense of multiple perspectives, orchestrating the process, supervisory relationship dynamics, and personal dispositions and characteristics. Results indicated that counselors-in-training experienced compounded benefits and challenges. Implications for supervisors, supervisees, and counselor education programs are provided.