Background: Breastfeeding mothers commonly experience nipple pain accompanied by radiating, stabbing or constant breast pain between feeds, sometimes associated with pink shiny nipple epithelium and white flakes of skin. Current guidelines diagnose these signs and symptoms as mammary candidiasis and stipulate antifungal medications. Aim: This study reviews existing research into the relationship between Candida albicans and nipple and breast pain in breastfeeding women who have been diagnosed with mammary candidiasis; whether fluconazole is an effective treatment; and the presence of C. albicans in the human milk microbiome. Method: The author conducted three searches to investigate (a) breastfeeding-related pain and C. albicans; (b) the efficacy of fluconazole in breastfeeding-related pain; and (c) composition of the human milk mycobiome. These findings are critiqued and integrated in a narrative review. Results: There is little evidence to support the hypothesis that Candida spp, including C. albicans, in maternal milk or on the nipple-areolar complex causes the signs and symptoms popularly diagnosed as mammary candidiasis. There is no evidence that antifungal treatments are any more effective than the passage of time in women with these symptoms. Candida spp including C. albicans are commonly identified in healthy human milk and nipple-areolar complex mycobiomes. Discussion: Clinical breastfeeding support remains a research frontier. The human milk microbiome, which includes a mycobiome, interacts with the microbiomes of the infant mouth and nipple-areolar complex, including their mycobiomes, to form protective ecosystems. Topical or oral antifungals may disrupt immunoprotective microbial homeostasis. Unnecessary use contributes to the serious global problem of antifungal resistance. Conclusion: Antifungal treatment is rarely indicated and prolonged courses cannot be justified in breastfeeding women experiencing breast and nipple pain. Multiple strategies for stabilizing microbiome feedback loops when nipple and breast pain emerge are required, in order to avoid overtreatment of breastfeeding mothers and their infants with antifungal medications.