This generic qualitative research study aimed to understand how clinical supervisors have supervised counselors grieving a personal loss. The present research on this topic shows that grief-related education and training are lacking in the field of counselor education and supervision, leading grieving counselors to feel unsupported and supervisors to feel ill-prepared to supervise a grieving clinician. This study sought to answer the research question: What are clinical supervisors' experiences supervising counselors who are grieving a personal loss? To answer the research question, the researcher utilized criterion and snowball sampling to obtain data from ten participants using open-ended semi-structured interviews. The study's theoretical orientation was rooted in Stroebe and Schut's (1999) Dual Process Model of Coping with Bereavement, which informed the interview questions and data analysis. The qualitative data from the interviews included the participant's experiences supervising counselors grieving a personal loss. Braun and Clarke's (2006) six-step thematic analysis was utilized to analyze the data and identify themes and subthemes. Results revealed six themes and nineteen subthemes that involved supervisors feeling unprepared for supervisee grief, that supervisee's meaningful relationships contribute to better supervision outcomes, supervisor-supervisee collaboration, and systemic support are necessary to accommodate supervisee grief, supervisors had to fill in the blanks when applying grief counseling to supervision, supervisor lack of grief advocacy exacerbates supervisee grief, and supervisors feeling unsure of how complex supervisee grief can be. This data may contribute to research demonstrating grief's impact on a counselor's clinical functioning and advocating for supervisors to receive adequate grief training. The results may also advocate for grief education and training to be incorporated into counseling programs and supervisor training. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]