Single Flight Probability of Failure (SFPOF) has been the recommended risk measure for probabilistic damage tolerance analysis for several decades. The definition of SFPOF has not been standardized, and the lack of benchmark example calculations makes it difficult to validate software which includes calculation of SFPOF. In this work we present our interpretation of SFPOF along with a Monte Carlo scheme for calculating SFPOF via straightforward simulation. We demonstrate these concepts through several illustrative examples from the documentation of PRobability Of Failure (PROF) – a popular probabilistic damage tolerance analysis software. We show that PROF v3.1 gives an estimate of SFPOF that is very conservative compared to our Monte Carlo solution. Finally, we describe how our simulation scheme can be extended to broaden the scope of the problem beyond the capabilities of available software, providing the means to benchmark future software which includes calculation of SFPOF.