Currently, metal working fluids (MWFs) are the standard coolants applied in grinding processes, avoiding the formation of surface cracks, burning, and residual tensile stresses. Due to sustainability-related issues, alternatives to MWF have been extensively researched. A few of these alternatives include minimum quantity lubrication (MQL), dry grinding, and the application of cryogenic fluids. Regarding cryogenic coolants, the usual approach consists of directing a cryogenic jet at the cutting zone, whereas pre-cooling has been a less explored strategy. The pre-cooling strategy aims to reduce the workpiece’s temperature below cryogenic temperatures beforehand, followed by dry machining, resulting in lower peak temperature values compared to regular dry machining. The application of cryogenic pre-cooling in cylindrical plunge grinding has been tested, and it has been claimed that its effectiveness is tied to the ratio between the volume and surface area of the workpiece. As a follow-up study, this work aims to evaluate both experimentally and through thermal simulations how the volume-to-surface ratio influences the thermal behavior of the workpiece as well as its dimensional accuracy. More specifically, two cylindrical AISI 4140H workpieces with different volume-to-surface ratios were ground, temperature measurements were performed at depths of 2 mm and 4 mm below the external surface, electric power consumption during grinding was also monitored and the initial and final diameter of the workpieces were measured. Furthermore, thermal simulations were also conducted to evaluate the temperature at the surface during the process, assuming ideal conditions. It was found that larger workpieces are able to more easily conserve cryogenic temperature given their higher heat capacity at the expense of worse dimensional accuracy due to higher thermal contraction. Workpieces with smaller volume-to-surface, on the other hand, present lower heat capacity and higher dimensional accuracy. Therefore, larger workpieces demand more technical know-how in order to account for the contraction and expansion of the workpiece during grinding, while smaller workpieces require better thermal insulation to reduce heat transfer between the workpiece and environment, keeping cryogenic temperatures for a longer period.