This article presents the results of the studies on negative streamer propagation in a point-to-sphere electrode system with a pressboard barrier placed between them. The proposed electrode system gave the opportunity to assess the influence of the insulating barrier on streamer development in the conditions close to the actual transformer insulating system where the liquid gap is typically divided in parts by using pressboard barriers. The studies were performed for five commercial dielectric liquids. Among them two were biodegradable synthetic esters and two were biodegradable natural esters. Mineral oil, as the fifth liquid, was used for comparison. The measurements were based on electrical and optical experimental techniques. From the results obtained it may be concluded that, independently of the liquids tested, the electrical strength of the insulating system considered was increased by about 50%. In the case of streamer development assessed using photomultiplier-based light registration it is not possible to indicate clearly which of the liquids tested is better under the conditions of the experiment. In all cases streamers always developed slowly (2nd mode) at all voltage levels applied during the studies. In turn, the intensity of the discharge processes, comparing the same voltage levels, was mostly higher when streamers developed in ester liquids, however, the differences noticed were minimal.