Insurance Portfolio Analysis (IPA) is the process of comparing multiple, potentially overlapping insurance portfolios with an eye to detecting and characterizing redundancies and gaps in coverage. Unfortunately, insurees usually do not have the time or patience to compare policies from multiple insurance providers, and they often do not have the legal background needed to understand the complex legal wording of the contracts associated with those policies. Past work has shown that, by encoding policies as logic programs, it is possible to automatically determine compliance of specific claims with a policy’s terms and conditions. In this paper, we show that it is also possible to automatically analyze multiple-policy portfolios for gaps and redundancies by assessing coverage over multiple hypothetical claims. We formalize the process of IPA and show how to use well-studied techniques for logic program containment testing to automate the process.