On-line condition monitoring is a useful tool for maintaining and extending the longevity of power transformers. An intelligent diagnostic system is desirable for operational safety and reliability. Bringing these concepts together results in a powerful support tool for engineers, reducing the volume of data to deal with, and making the data more meaningful. This paper describes how a multi-agent system for diagnosing the cause of transformer partial discharge activity was coupled with a method of UHF partial discharge monitoring, creating an on-line condition monitoring system. The challenges presented by the on-site environment are discussed, along with the implications for the complete system.