Although a large body of literature recognises the impact of parent-teacher relationships on infant everyday experiences, less is known about the emotional experience and associated expectations of the adults themselves during earliest transitions. In the context of a multi-site international investigation across five countries -- Brazil, Finland, Scotland, New Zealand, and the United States -- the present paper examines teacher and parent interviews to reveal expectations prior to and after the transition to ECEC, highlighting the associated emotions that arise during this process. Irrespective of whether expectations are met, parents universally express insecurities and fears in relation to the transition. Parents are aware of the impact that the various aspects of the ECEC setting have on their child, and acknowledge difficulty in relinquishing control of the care of their child. Despite these concerns, parents consistently articulate their strong trust in the institution and the professional expertise of the staff. Correspondingly, teachers are keenly aware of the importance of their role in supporting families, and hold certain expectations for how the transition experience will play out accordingly. Regardless of country of context, the study shows that clear communication surrounding both centre and parental expectations establishes high levels of trust and ameliorates anxiety. Teacher-parent dialogues concerning routines, preferences, and anticipations are seen as pivotal in supporting a positive transition for all.