We conducted a cross-sectional survey of pharmacists in clinical settings to assess the status and extent of challenges experienced by pharmacists in providing drug information to pregnant and breastfeeding women. The survey was completed anonymously via the internet using a structured questionnaire. The survey items included basic respondent characteristics, their experiences, attitude toward providing information to pregnant and breastfeeding women, and efforts toward obtaining relevant knowledge. Out of the 1,000 participating pharmacists, 96.8% received inquiries about pregnancy and breastfeeding. However, 92.5% of them recognized that the consultations they provided to pregnant and breastfeeding patients were not sufficient. The reasons for the sentiment were as follows: a lack of basic knowledge regarding pregnancy and breastfeeding and the effects of medications on pregnancy and breastfeeding (37.9% and 37.7%, respectively), a feeling that it is difficult to select appropriate information to share with patients (32.1%), lack of detailed information in the drug package insert (26.0%), lack of opportunities to learn about drug treatment during pregnancy and breastfeeding (20.9%), and the notion that pregnancy and breastfeeding are delicate and difficult topics to discuss (19.8%). While most pharmacists provided consultations regarding pregnancy and breastfeeding, only 7.5% felt that they provided sufficient consultations on this topic. Some pharmacists were concerned about their limited knowledge of pregnancy and breastfeeding. They also had difficulty addressing pregnancy and breastfeeding-related subjects, and communicating with pregnant and breastfeeding women. Pharmacists should advance their education by including elements regarding informed choice and make use of appropriate sources of information.