Drug-induced anaphylaxis (DIA) is a highly paradoxical disorder involving a fatal response to medicines prescribed for therapeutic purposes. This study aimed to improve the awareness on DIA and to prevent errors through an analysis of lawsuit judgments. Sentenced judgments involving DIA from 1998 to 2017 using the database of the Korean Supreme Court Judgment System were collected. General characteristics, results, and recognized negligence of DIA litigation cases were analyzed. Of 27 lawsuit cases included, antibiotics (n = 6, 22.2%), radiocontrast media (n = 6, 22.2%), and non-steroidal anti-inflammatory drugs (n = 5, 18.5%) were the most common drugs that had caused DIA. Cardiac arrest was reported in 23 cases (85.2%). The median time interval from drug administration to diagnosis and from diagnosis to cardiac arrest were 7 (interquartile range, IQR = 0–35) and 5 minutes (IQR = 0–33), respectively, suggesting insufficient time to cope with anaphylaxis. Consequently, either death (n = 18, 66.7%) or ischemic brain injury (n = 9, 33.3%) occurred in all cases. Violation of duty of care was recognized in 19 cases (70.4%) with median awarded amount of $106,060 (IQR = $70,296–$168,363). The recognized negligence included inadequate observation after drug administration (n = 6), delayed or missed epinephrine administration (n = 6), ignoring a history of allergy or drug hypersensitivity (n = 6), and prescription error (n = 5). It is necessary to improve the awareness on DIA, because making a trivial error in any process of history taking, drug prescription and administration, observation, and/or emergency treatment may have fatal consequences that can lead to indemnity.