Effective communication about preventive oral health is a core skill for dental practitioners. In the UK, newly qualified dentists complete a one-year Foundation Training Programme in general practice. This study investigated the challenges and enabling factors that Foundation Dentists encounter when discussing oral health with parents and caregivers of children aged 0–11 years. Approximately 100 Foundation Dentists from the Yorkshire and Humber region took part in focus group discussions. These sessions explored how they and their broader dental teams approach oral health guidance for young children. The collected data were examined using thematic analysis. Analysis revealed five central themes influencing oral health discussions: (1) Gaps in understanding parenting and child development; (2) Parents’ willingness to engage; (3) Drivers for behavior change; (4) Variability and clarity of information shared; and (5) Organizational constraints within the National Health Service (NHS) general practice framework. A comprehensive, multi-layered training approach is recommended to better equip Foundation Dentists for preventive oral health conversations with children and their caregivers. Enhancing these skills may strengthen practitioner–patient interactions and support meaningful behavior change, ultimately contributing to improved oral health outcomes in children.