Background: The omission of time-critical medication doses may result in poor patient outcomes. There are few publications about the influence of electronic medication management (EMM) systems, including automated dispensing cabinets (ADC), on timely medication administration. The study aimed to evaluate the influence of EMM systems, including ADCs, on timely medication administration 6 and 30 months after EMM implementation, focussing on preventable time-critical medication dose omissions and documented reasons for not administering a dose. Methods: Data on doses of regular inpatient medications not administered were obtained from electronic medication records (EMR) over 1 week in March 2019 and 4 weeks in March 2021. An omission was a dose not administered before the next due dose. Time-critical medications were defined using the health service’s guidelines. Reasons for doses not being administered were obtained from nursing documentation in the EMR collated from digital health reports. Reasons for time-critical medication doses not given were defined as ‘valid’ or ‘preventable’. Results: In 2019 and 2021, 620 and 2524 patients with 44,756 and 146,940 scheduled medication doses were reviewed. Of these, 4385 (9.8%) and 19,610 (13.4%) doses were not administered. In 2019 and 2021, there were 593 (1.3%) and 1811 (1.2%), p < 0.0001, time-critical doses not administered. Preventable time-critical dose omissions decreased from 0.20% in 2019 to 0.15% (p = 0.015) in 2021. Wards with ADCs had a significantly lower rate of time-critical dose omissions compared to those without ADCs (1.1% vs 1.3%, p = 0.014). Conclusion: With the introduction of an EMM system, there was a decrease in the rate of time-critical medications not administered, including a reduced rate of preventable omissions over the 24-month period. Regular assessment of time-critical medication administration will help target patient safety improvements.