PhD supervision is generally deemed a rewarding experience as supervisors and students embark on an academic journey together. Pursuing a PhD in a 'foreign' context inevitably brings forth distinct opportunities and challenges for students and their supervisors. Using Interpretative Phenomenological Analysis, this qualitative study of supervisors and PhD students examines the cross-cultural facets of doctoral supervision in the light of Urie Bronfenbrenner's bio-ecological theory of human development and its underpinning explanation for supervisory processes and learning orientations. Undertaken in the Danish context, our paper highlights exemplars of contrasting supervisors' and PhD students' experience in relation to academic and psychosocial adaptations. This research strongly endorses that supervisors' appreciation of the intertwined link between academia and society combined with a positive view of their role in bridging academic cultures can powerfully complement students' adjustments and subsequently make a qualitative difference towards a more fulfilling and meaningful academic journey together.