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Supervision is central to psychotherapist training, particularly within the psychodynamic paradigm, where professional development unfolds through relationship. This qualitative study explores how supervisors and supervisees experience the supervisory relationship during the initial phase of psychodynamic psychotherapy supervision (within the first 10 sessions). Six supervisor–supervisee dyads from Lithuania participated in semistructured interviews, with data analyzed using reflexive thematic analysis. Supervisees emphasized the need for emotional safety, pedagogical competence, and space to reflect on difficult emotions. They valued warmth, flexibility, and the ability to be vulnerable without judgment. Supervisors highlighted the importance of fostering openness, managing defensiveness, and adapting to each supervisee's pace. They also reflected on their own task of building mutual understanding and providing the necessary conditions for supervisees early in the process. The findings underscore the emotional and interpersonal complexity of early supervision, shaped by relational dynamics and individual traits. Implications are offered for cultivating supportive and growth-oriented supervisory relationships in psychodynamic and psychoanalytic training contexts.