Background: Pregnancies following perinatal loss present emotional and clinical challenges that require individualized care. While awareness of the psychological vulnerability of bereaved parents is increasing, the perspectives and preparedness of healthcare professionals (HCPs) are still under-investigated. Methods: The UNSURENESS study involved a national cross-sectional web-based survey conducted between August 2023 and February 2024. The questionnaire explored sociodemographic data, professional experience, training in perinatal loss care, communication approaches, and clinical decision making. Results: Two hundred female HCPs participated (midwives 78.0%). One-third had received specific training on managing pregnancies after perinatal loss. On a 0–4 Likert scale, participants emphasized the importance of addressing the previous loss (M = 3.82; SD = 0.03) and building a trusting relationship with parents (M = 3.78; SD = 0.04). Providing comprehensive information (M = 3.59; SD = 0.05) and promoting shared decision making (M = 3.72; SD = 0.04) followed closely. The most challenging tasks included responding to parental fears (M = 3.37; SD = 0.75) and offering reassurance (M = 3.06; SD = 1.06). Clinical decisions were primarily driven by continuity of care (M = 3.70; SD = 0.56) and parental preferences (M = 3.63; SD = 0.57), rather than national guidelines (M = 3.16; SD = 0.82) or research evidence (M = 2.86; SD = 0.94). Conclusions: HCPs are aware of the psychosocial complexity involved in these pregnancies but often lack specific training. There is a clear need for trauma-informed interventions and national guidelines to better support both professionals and bereaved families.