The development of overload management systems for distribution transformers offers new opportunities for improving the reliability of distribution systems. It allows network planners to optimize the system resource utilization and investment cost. Such an improvement in the flexibility of the distribution network is only possible if the operator has more accurate knowledge of the realtime conditions of distribution transformers. In this paper, we present an improved overload decision system for distribution transformers using realtime monitoring data. Our study can be categorized into two parts: (a) improvement in the criteria for judging the overload conditions of distribution transformers and (b) development of an overload evaluation system using realtime monitoring data. In order to determine the overload criteria, overload experiments are performed on sample transformers; the results of these experiments are used to define the relationship between the transformer overload and the increase in the top-oil temperature. To verify the accuracy of the experimental results, field tests are performed using specially manufactured transformers, the loads and top-oil temperatures of which can be measured. For arriving at online overload decisions, we propose methods whereby the measured load curve can be converted into an overload characteristic curve and the overload time can be calculated for any load condition. The developed system is able to evaluate the overload for individual distribution transformers and calculate the losses using realtime monitoring data.