Counsellor educators face complex challenges in the advancement of the counselling profession internationally. One way the counselling profession in Ukraine has been developed is through the use of cross-cultural engagement between local supervisees and U.S.-trained international supervisors. This qualitative study examined the phenomenon of the cross-cultural supervisory experiences of twelve participants involved in transnational distance supervision among Ukrainian supervisees, and their U.S.-trained, non-Ukrainian supervisors. Semi-structured interviews were used to elicit participants’ descriptions of their supervisory experiences. Participants identified commitment to the supervisory relationship, the importance of felt supervisor support, shared resources to promote counsellor growth, and in-person meetings in the supervisee’s context prior to the start of the supervisory relationship as the most important aspects of supervision. The researchers highlight implications and propose recommendations for counsellor educators and supervisors desiring to implement cross-cultural or transnational supervision in different cultural contexts.