The authors substantiate the relevance of the tasks of developing methods ensuring the greatest efficiency of implementing state land supervision and monitoring using automated procedures for the centralized formation of an annual inspection plan. The mechanisms of identifying natural objects, buildings and structures as potential ones included in the annual inspection plans on the mentioned issue are described. This meets many goals and, above all, the safety of land use, and eliminating negative processes of land degradation. Examples of using aerial photographs as the most significant practice at detecting violations in the field of land protection and use are given. To a greater extent, this applies to real estate cadastre objects with simpler geometric shapes, e.g. boundaries of land plots, buildings. The methods of comparing the geometric complexity of contours proposed in the study enable creating automated mechanisms and determine discrepancies between the actual and recorded characteristics of control objects, depending on the set goals and objectives. The expediency determining mechanisms of automated search for features with signs of land legislation violations are presented. It simplifies the implementation of control measures and makes the inspection system itself more transparent. The purpose of the research was to study the possibility of applying the theory of geometric complexity in the implementation of a centralized system of state land supervision and monitoring. In this regard, we made an attempt to use Minkovsky metrics for simpler geometric structures in contrast to natural objects, as well as morphometric indicators to identify those where land legislation is not being followed. The relative criteria values of the real estate cadastre control’s compared objects’ geometric complexity are numerically determined and proposed