Background: Tongue-tie or ankyloglossia is a congenital condition that negatively affects breastfeeding. The thickened, tightened, or shortened frenulum affects the infant’s ability to suck and frequently results in sore and painful nipples. Although several studies have investigated outcomes associated with treatment of tongue-tie, none have investigated mothers’ experiences of breastfeeding an infant with tongue-tie. Objective: This study aimed to understand the breastfeeding experiences of women whose infants have tongue-tie. Methods: A hermeneutic phenomenological design was employed. Data were collected using focused interviews and, following transcription, were analyzed in the phenomenological tradition. Ten women who presented at a breastfeeding clinic with feeding problems, and were diagnosed with tongue-tie, were interviewed on 2 occasions. Results: The analysis revealed a common story of tension between the mothers’ expectations and the breastfeeding challenges they faced. Their journey was characterized by 6 distinct phases described in the following themes: Expectations; Something is wrong; Questioning, seeking advice, no real answers; Symptoms and perseverance; Approaching the wall—it’s all too much; and finally, Relief. Conclusion: The women in this study described a somewhat harrowing journey, which was at odds with the natural experience they had anticipated. They encountered health professionals who were found to have limited knowledge of tongue-tie and its potential effect on breastfeeding and were unable to provide appropriate advice concerning their breastfeeding difficulties. However, following treatment with frenotomy, their breastfeeding experience improved dramatically. The reported incidence of tongue-tie is significant, and early identification and prompt and effective management would contribute to improved breastfeeding.