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Background Closed Loop Medication Management System (CLMMS) is an end-to-end medication delivery system comprising seamless interfaces, independent verification processes and information feedback to improve safety and quality. Aim Following implementation of a CLMMS at an academic medical centre in Singapore, this study was conducted to identify any safety issues and areas for quality improvement. Method A direct observational study was conducted in the wards, inpatient pharmacy and unit-dose satellite pharmacy. The numbers and types of medication errors in prescribing, supply and administration were observed and recorded to calculate the error rate. Events that have the potential to cause errors were also observed. Results The prescribing error rate was 1.3% and the most common prescribing error was dose error. Supply error rate was 0.7% in which labelling error occurred most frequently. Workflow issues were the most common occurrences that could potentially cause prescribing and supply errors. The administration error rate was 7.3%, and wrong drug preparation technique was most commonly seen. Improper procedure in the use of personal digital assistant was the most common event that could potentially lead to an administration error. Conclusion This study was instrumental in identifying important medication safety gaps in order to improve the inpatient CLMMS. Although a failure mode and effects analysis was performed prior to implementation of the system, unintended error types may still be introduced. Hence a post-implementation audit is necessary to address such issues to ensure that the CLMMS objective of improving medication safety is achieved.