Medications are commonly used during pregnancy; in fact, female patients take an average of 2.9 medications during pregnancy. Due to this high prevalence, malpractice litigation poses a high legal risk to dermatologists who prescribe medications to female patients who are or may become pregnant. This article introduces the medicolegal risks involved in prescribing dermatological medications to a pregnant patient and discusses ways for a dermatologist to mitigate those risks. International safety classification systems are reviewed, and potential high risk dermatologic medications prescribed in acne, psoriasis, atopic dermatitis, and connective tissue disease are discussed. In addition, the article summarizes resources available to patients as well as the important elements for dermatologists to include when documenting their discussion with the patient in the medical record. Semin Cutan Med Surg 32:209-216 © 2013 Frontline Medical Communications