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Bootstrapping can account for uncertainty in propensity score (PS) estimation and matching processes in 1:1 PS‐matched cohort studies. While theory suggests that the classical bootstrap can fail to produce proper coverage, practical impact of this theoretical limitation in settings typical to pharmacoepidemiology is not well studied. In a plasmode‐based simulation study, the authors compared performance of the standard parametric approach, which ignores uncertainty in PS estimation and matching, with two bootstrapping methods.