The main aim of the present study is to explore the use of synthetic ester fluid as a transformer insulant. For this, the performance of thermally aged synthetic ester is investigated using corona inception voltage (CIV) measurement, fluorescent analysis, and dielectric spectroscopic studies. Then a fuzzy model is introduced to correlate the outcome of these studies to predict the key performance index and lifetime estimation of insulation structures. CIV tests for the thermally aged ester fluid, under AC voltage show 53.2% and 34% reduction in inception values due to ageing time and ageing temperature respectively. Furthermore, the effect of magnetic field on the performance of thermally aged ester is also studied and a drastic reduction of 54.3% and 39.4% respectively in CIV is observed. Statistical studies also indicate accelerated degradation of the insulation performance under the influence of the magnetic field, showing high scatter in CIV data indicated by decreasing beta values. Other studies such as fluorescent spectroscopy depict progressive shifts in fluorescence maxima and a decrease in emission intensity with ageing. Dielectric spectroscopy results show a manifold increase in dissipation factor due to thermal ageing. A fuzzy monitoring tool uses spectral data as input and at the output indicates the level of deterioration. The Rule-base of the model is framed using dielectric study.