The oil pipeline transportation of highly waxy oils when it is cold is accompanied by the deposition of paraffins in the inner surface of the pipeline. This study of the initial properties of the oil; the composition, structure, and nature of the components of normal alkanes in oil; and their influence on the aggregative stability of the resulting system makes it possible to find the best solutions to optimize the conditions of oil transportation with the lowest energy costs. This study shows that, according to the content of solid paraffin (14.0–16.2%), the oils of the Kumkol group of fields in Kazakhstan are highly waxy. They are characterized by high yield loss temperature values (+9–+12 °С), which also correlate with the values of the rheological parameters (t0 1.389 Pa, 3.564 Pa). The influence of the temperature and shear rate on the shear stress and effective viscosity of the initial oils was studied. At temperatures below 20 °C, depending on the shear rate, there is an increase in the effective viscosity values (0.020 Pa∙s, 0.351 Pa∙s). The influence of the nature of solid hydrocarbons on the parameters of the paraffinization process and of the intensity of the paraffinization of the metal surfaces was studied. Our study shows that the main share of n-alkanes in the Kumkol and Akshabulak oils falls on paraffins of the C15–C44 group. The greater the temperature difference between the oil and the cold steel surface (≤40 °С), the lesser the amount of asphalt–resin–paraffin deposits (ARPDs) that fall out on the surface of the rod, although the content of long-chain paraffins prevails in these ARPDs. At the same time, the consistency of the released asphalt–resin–paraffin deposits (ARPDs) becomes denser, which makes their mechanical removal more difficult. Furthermore, the results of this study of the cooling rate shows that the rapid cooling of oils leads to the formation of a large number of crystallization centers, which leads to an increase in the values of the yield loss temperature and kinematic viscosity of the oils.