During the study of forensic medical examinations conducted in 2013—2022 in cases related to poor-quality dental care, the main features of the implementation of expert assessments were identified. The most common (in 46% of cases) assessment of comprehensive dental care is carried out. In 6% of cases, claims are made to 2—5 medical organizations at once. In 15—20% of cases, during the forensic medical examination, the condition in the oral cavity has already been changed by subsequent dental treatment. In the course of the study, it was determined that payments from dental organizations are on average 10 times higher than the cost of treatment and account to about 40% of the amounts requested by patients in claims. In 15% of cases, forensic medical examination was carried out on dental care provided within the framework of state guarantees of free medical care. Claims for compensation for moral damage were contained in 97% of cases, in 56% of cases the court confirmed their validity. The growth rate of cases where claims for compensation for moral damage were satisfied for 10 years amounted to 36%. The amount of compensation payments has increased. The revealed features of judicial practice in dentistry necessitate the development of objective, evidence-based, reproducible assessments and the introduction of evaluation criteria in clinical recommendations for the relevant nosology.