The urban area’s soil cover is modified mainly by human activity. This study aimed to reveal the transformation of natural Chernozems under anthropogenic factors such as shielding, overlap by man-made horizons, compaction, and heavy metal and oil product pollution in urban conditions. The study employed a combination of field observation, morphological feature descriptions, soil sampling, and analysis of soil chemical characteristics (organic carbon content, total chemical composition, and petroleum product content). Three primary pathways of Chernozem transformation in the Rostov agglomeration were revealed: (i) stagnation of soil formation under the burial layer of the Urbic horizons, with the formation of Urbic Technosol (Molic) and Calcic Chernozem Novic (Technic); (ii) preservation under a solid impermeable surface, forming different sealed urban soils, Ekranic Technosol; and (iii) intensification of the main soil-forming processes under forests leading to the formation of rich-humus highly leached (strongly alkali) Calcic Chernozem. The separate transformation pathway is characterized by chemo transformation due to chemical contamination by zinc and petroleum products. Even if the external morphological features of Chernozem do not undergo obvious changes, the transformation will occur at the level of the soil-absorbing complex and soil solutions, leading to the formation of Urbic Technosol (Toxic).