In general, patients receiving certain drugs, such as antiplatelet and anticoagulant drugs, require drug holidays before surgery. In oral surgery, several drugs may require drug holidays. Among oral surgeries, mandibular third molar extraction is performed most frequently. To date, several postoperative complications need to be considered. Various complications of mandibular third molar extraction have been reported, including post-extraction infection, post-extraction bleeding, swelling, difficulty in opening, nerve injury, dry socket (alveolar osteitis), and osteonecrosis of the jaw. Among them, post-extraction bleeding, dry socket, and osteonecrosis of the jaw have been reported as drug-induced post-extraction complications; therefore, drug holidays may be recommended in such cases. Recently, with the aging of dental patients, there are more opportunities to perform extractions in patients with multiple medical histories or those who take many medications. Therefore, it is necessary to thoroughly check the medications before extraction. This section discusses the concept of drug holidays in relation to post-extraction complications strongly associated with the drugs patients take during mandibular third molar extraction: post-extraction haemorrhage, osteonecrosis of the jaw, and dry socket.