A prototype data acquisition and processing system is developed for evaluating the insulation condition of a power transformer winding in real-time. The Transformer Insulation Condition Monitoring System (TICMS) evaluates the insulation condition by calculating the winding transadmittance function. The winding transadmittance function is used to fingerprint the insulation system and provides a means of monitoring its condition. The use of a transfer function for evaluating the insulation condition of a power transformer winding was proposed by Malewski and Poulin in 1988 [6, Chapter 1]. The work described in this thesis extends their work in a number of important areas and makes the following contributions to the state-of-the-art. Firstly, ...