Rubber is one of the most used materials in the world; however, raw rubber shows a relatively very low mechanical strength. Therefore, it needs to be cured before its ultimate applicatios. Curing process specifications, such as the curing time and temperature, influence the material properties of the final cured product. The transient radar method (TRM) is introduced as an alternative for vulcanization monitoring in this study. Three polyurethane-rubber samples with different curing times of 2, 4, and 5.5 min were studied by TRM to investigate the feasibility and robustness of the TRM in curing time monitoring. Additionally, the mechanical stiffness of the samples was investigated by using a unidirectional tensile test to investigate the potential correlations between curing time, dielectric permittivity, and stiffness. According to the results, the complex permittivity and stiffness of the samples with 2, 4, and 5.5 min of curing time was 17.33 ± 0.07 − (2.41 ± 0.04)j; 17.09 ± 0.05 − (4.90 ± 0.03)j; 23.60 ± 0.05 − (14.06 ± 0.06)j; and 0.29, 0.35, and 0.38 kPa, respectively. Further statistical analyses showed a correlation coefficient of 0.99 (p = 0.06), 0.80 (p = 0.40), and 0.92 (p = 0.25) between curing time–stiffness, curing time–permittivity (real part), and curing time–permittivity (imaginary part), respectively. The correlation coefficient between curing time and permittivity can show the potential of the TRM system in contact-free vulcanization monitoring, as the impact of vulcanization can be tracked by means of TRM.