It is extremely difficult to predict the initiation time of cracking due to a large time spread in most cracking experiments. Thus, probabilistic models, such as the Weibull distribution, are usually employed to model the initiation time of cracking. Therefore, the parameters of the Weibull distribution are estimated from data collected from a cracking test. However, although the development of a reliable cracking model under ideal experimental conditions (e.g., a large number of specimens and narrow censoring intervals) could be achieved in principle, it is not straightforward to quantitatively assess the effects of the ideal experimental conditions on model estimation uncertainty. The present study investigated the effects of key experimental conditions, including the time-dependent effect of the censoring interval length, on the estimation uncertainties of the Weibull parameters through Monte Carlo simulations. The simulation results provided quantified estimation uncertainties of Weibull parameters in various cracking test conditions. Hence, it is expected that the results of this study can offer some insight for experimenters developing a probabilistic crack initiation model by performing experiments.