This paper provides a literature review of methods and modeling techniques to estimate the cost of power system outages, along with the value of outage mitigation or system resilience. Regulators, policymakers, and infrastructure owners have a growing need to understand the methods for estimating the benefits of resilience improvements of electric infrastructure against natural and man-made disasters. There is a broad literature that estimates the cost of short-duration outages and a small but developing literature on estimating the cost of long-duration outages. This article reviews the models used to estimate the cost of outages and discusses their relative strengths. Additionally, this paper identifies key questions from stakeholders regarding resilience investment and maps them to the relevant models that would help answer them. We include recommendations for future work to include recent advances in regional economic modeling that can estimate region and demographic-specific costs and the distributional consequences of potential resilience projects.