Insulating barriers utilized in complex high voltage insulation systems has been exploited widely by manufacturers of power apparatus. Barriers have found utility in a variety of power apparatus for protection against direct lightning strokes, as an interface at the boundaries of composite insulation materials etc. Though investigations have been carried out by researchers on the breakdown characteristics, barrier position in the gap, influence of space charge etc these characteristics have been analyzed based on aspects pertinent to classical testing procedures only. Advent of high speed switching devices in power systems provides avenues to investigate the effect of insulation performance due to High Frequency High Voltage (HFHV) also. Further, uncharacteristic failures in oil filled distribution transformers have been reported indicated fast transients as the major cause for failures which was not revealed during classical laboratory testing. This research focuses on the influence and effects of solid insulating barriers placed in transformer oil due to HFHV in inhomogeneous fields. Test cell arrangement has been fabricated for carrying out experimental investigations to adhere international standards. Exhaustive experimentation has been performed to infer the influence of the position of barrier, nature of field and breakdown voltage, erosion characteristics of the barrier at an appropriate range of frequencies. A detailed comparison between HFHV and classical power frequency voltage has been carried out. The nature of ionization at the barrier interface and the subsequent increase in the breakdown voltage as explained by Double Electric Layer (DEL) theory has been cross validated. In addition, a study has also been carried out to assess and characterize the ageing of oil based on Dissolved Gas Analysis (DGA) analysis using Weibull distribution.