Problem: The health of women is dependent on midwifery workforce stability. Retaining new midwives is paramount, however without support, the early career can be a vulnerable time for midwives. Background: Midwives care for women who experience poor perinatal outcomes like stillbirth and neonatal death. Midwifery care in these sentinel events is complex. There is limited understanding of early career midwives’ experiences within these encounters. Aim: To understand the experiences of Australian early career midwives’ clinical encounters with perinatal grief, loss and trauma. Methods: A qualitative descriptive/exploratory study using in-depth interviews. Findings: Four themes were identified from interview data: (1) all eyes on the skills; (2) support is of the essence; (3) enduring an emotional toll; (4) at all times, the woman. Most participants had minimal exposure to perinatal loss as a student. As a result, most felt unskilled and unprepared for this as a new midwife. Discussion: Types and degrees of support varied in these encounters. Early career midwives who were well supported reflected positively on working with grief and loss. In contrast, inadequate or absent support had detrimental effects on participant wellbeing. Poorly supported encounters with death (intrapartum fetal, early neonatal, and maternal) in the early career period were significantly distressful, giving rise to mental and emotional distress. Conclusion: Pre-registration perinatal loss skill development and supported experiences are necessary for preparedness. Continued education, formalised debriefing and mentoring, institutional philosophies which promote collegial ethics of care, and the expansion of continuity of midwifery care models will improve new midwives’ experiences.