The health benefits of breastfeeding are well documented and current recommendations are that women should breastfeed their child for two years and beyond. Despite this the UK has the lowest initiation breastfeeding rates in the world. Additionally, a considerably small percentage of women who do successfully initiate go on to breastfeed past infancy. This could in part be explained by the lack of support women receive when breastfeeding an older child. In this study we provide insight into women's experiences of healthcare interventions during the transition from breastfeeding an infant to a toddler. We conducted semi-structured interviews with 24 women with experience of breastfeeding at least one child past the age of twelve months. We used a theory driven thematic analysis to identify pertinent themes that ran through the interviews. As mothers progressed through their breastfeeding journey they faced increased social stigma. They also experienced a change in attitudes from healthcare professionals as support was replaced by judgement. This negatively impacted upon trust in healthcare professionals and the advice they offered. In response, the women turned to volunteering organizations and closed social media groups for emotional support and healthcare advice. These women experienced specific issues regarding breastfeeding in toddlerhood as opposed to infancy. They needed specialized interventions tailored for this. Social media was highlighted as a useful platform for supporting women who breastfeed beyond infancy. It allowed these women to feel part of a supportive international community and gain access to practical advice. Healthcare professionals should explore ways to engage in digital platforms to provide support to mothers' breastfeeding beyond infancy.