Background: Taking medication during breastfeeding is often a major concern for mothers. Knowledge, representations, and attitudes condition a mother’s behavior in this situation. Healthcare professionals, whose medication advice for breastfeeding women is often described in scientific literature as inappropriate, play a major role in counseling mothers. Healthcare professionals’ perceptions of mothers’ behaviors regarding medication use during breastfeeding may influence mothers’ behaviors. Research Aim: The aim of this study was to identify healthcare professionals’ perceptions of breastfeeding women’s knowledge, representations, and attitudes and behaviors about medication use. Method: A cross-sectional, prospective qualitative design was used. Semistructured interviews were conducted with a broad array of healthcare professionals ( N = 20) in different practice settings in the Angers area (France). Thematic analysis of the interview transcripts was carried out using the planned behavior theory of Ajzen. Results: Seventy themes concerning medication use while breastfeeding were identified and then combined into 8 categories. Healthcare professionals perceived that maternal behaviors regarding medication were mostly focused on the child’s safety and were linked to poor knowledge and negative representations, attitudes, and feelings toward medication. Healthcare professionals also perceived significant negative influences from the mother’s friends and family in regard to breastfeeding. Relationships between healthcare professionals and women were problematic when it came to drug use during breastfeeding. Conclusion: Taking into account healthcare professionals’ perceptions of maternal behavior will help improve education for these professionals. Indeed, knowing precisely what difficulties are met by healthcare professionals when they encounter medication use during breastfeeding can help educators improve training for these professionals.