In this report, we present a case series involving four patients placed on the Clinical Institute Withdrawal Assessment for Alcohol, Revised (CIWA-Ar) protocol for alcohol or sedative-hypnotic withdrawal syndromes, who developed delirium on sustained or increasing symptom-triggered benzodiazepine dosages. In each of the four cases, delirium was not present on admission and resolved in the hospital itself with fixed benzodiazepine tapers. Cases were selected from an electronic medical record database of patients admitted to a United States-based university hospital and placed on CIWA-Ar between 2017 and 2018. This case series illustrates the major limitations of CIWA-Ar including its subjective nature, its susceptibility to inappropriate patient selection, and its requirement for providers to consider alternative etiologies to alcohol and benzodiazepine withdrawal syndromes. These cases demonstrate the necessity of considering other assessment and treatment options such as objective alcohol withdrawal scales, fixed benzodiazepine tapers, and even antiepileptics. An effective systems-based approach to overcoming these challenges may include setting time limits on CIWA-Ar orders within the electronic health record (EHR) system.