Delivery of pain-free dental treatment is the ultimate goal for clinicians, and the hoped-for result by patients. Thanks to the optimised use of local anaesthesia and high standards of clinical training, this goal is frequently achieved. Research also tells us that the incidence of persistent pain following dental procedures, while relatively low, is not zero. Given the number of procedures we perform as dentists, the number of patients affected with post-treatment pain is still substantial. Moreover, persistent pain is not exclusive to dentistry, but is a risk for all surgical interventions. When this pain lasts over six months it has been labelled persistent or chronic post-surgical pain (CPSP), and as expected it has a detrimental effect on the patient’s quality of life. While all persistent pain is vexing, it is especially true for persistent orofacial pain. It creates increased levels of stress, anxiety and confusion for the patient, which in turn may place a strain on the dentist-patient relationship. On occasions, patient dissatisfaction may even result in medicolegal litigation. This article describes some of the common clinical scenarios associated with chronic pain after dental procedures. Known risk factors are also discussed and recommendations are made so that clinicians might identify those at risk prior to an invasive procedure, and then possibly prevent post-surgical pain.