During the operation process of high-voltage insulators, the characteristics of assessing their technical state are evaluated by using remote contactless monitoring and by subsequent forecasting of their residual life based on the developed set of diagnostic parameters of critical defects. Special attention is paid to the challenges of the practical application for remote contactless monitoring of high-voltage insulators’ current operating state. Measurements of characteristics for partial discharges on high-voltage insulators with various types of critical defects taken by electromagnetic and acoustic sensors are described. Based on the measurements, it was found that the unusual properties of the PD begin to manifest themselves starting from the intensities q ≥ 1.5–2 nC, and their maximum intensity can reach 5–7 nC. Up to PD intensities q ≤ 3 nC, most parameters of PD characteristics measured by electromagnetic and acoustic sensors correspond with an accuracy of 70–90%. It was found that for small defects with sizes d ≤ 300 μm in HVI, the PD intensity does not exceed 100 pC and depends little on the size of the defect. However, with an increase in the size of defects above 0.4–0.6 mm, a sharp rise in the intensity of the emerging VLPD begins.