Cherenkov light can improve the timing resolution of Positron Emission Tomography (PET) radiation detectors, thanks to its prompt emission. Coincidence time resolutions (CTR) of ~30 ps were recently reported when using 3.2 mm-thick Cherenkov emitters. However, sufficient detection efficiency requires thicker crystals, causing the timing resolution to be degraded by the optical propagation inside the crystal. We report on depth-of-interaction (DOI) correction to mitigate the time-jitter due to the photon time spread in Cherenkov-based radiation detectors. We simulated the Cherenkov and scintillation light generation and propagation in 3 × 3 mm2 lead fluoride, lutetium oxyorthosilicate, bismuth germanate, thallium chloride, and thallium bromide. Crystal thicknesses varied from 9 to 18 mm with a 3-mm step. A DOI-based time correction showed a 2-to-2.5-fold reduction of the photon time spread across all materials and thicknesses. Results showed that highly refractive crystals, though producing more Cherenkov photons, were limited by an experimentally obtained high-cutoff wavelength and refractive index, restricting the propagation and extraction of Cherenkov photons mainly emitted at shorter wavelengths. Correcting the detection time using DOI information shows a high potential to mitigate the photon time spread. These simulations highlight the complexity of Cherenkov-based detectors and the competing factors in improving timing resolution.