Calving-related losses (survival, health, and productivity of cows and calves) are known challenges for the dairy industry worldwide, and poor management practices can increase the risk of these losses. It is common to observe large variation within and between herds on the quality and quantity of calving-related records. The objective of the present study was to assess an application (APP) for hand-held smart devices to capture defined calving-related events in dairy herds. Calving events collected by personnel (n = 23) from 6 large dairy operations (range: 900–5,000 cows) were recorded. Calving personnel received the same training on calving management and use of the APP before collecting events. Immediately after training, personnel recorded calving events (n = 448) using the APP for 7 d. Personnel satisfaction with the APP and knowledge gained from the training were assessed. Calving personnel reported that the information provided during the training was relevant (agree = 14.3% and strongly agree = 85.7%) and of great immediate use (agree = 33.3% and strongly agree = 66.7%). The presented materials and demonstrations substantially increased (P < 0.05) the knowledge level of the participants by 23.7 percentage points from pre- to posttest scores. The APP accurately captured (100%) calving events and integrated multiple metrics with personnel performance (accounting for the effect of shift change) such as the dam (e.g., date-time of calving), colostrum (e.g., timing, quality, and quantity) and newborn calf (e.g., presentation, vigor). The follow-up assessment with participants revealed that the APP was easy to use (91.3%) and that they would like to keep using it (100%). Dairymen, consultants, and veterinarians often trouble-shoot calving related losses within-herd; however, the lack of meaningful records makes it difficult to implement effective corrective measures. It is important to note that the timing and accuracy of data is always dependent on the willingness of the individual recording the information. However, this effective and easy-to-use tool requires minimal personnel training. These findings showed that decision-makers can monitor calving events and losses (magnitude and time) at the farm level accounting for the effect of management.