Estimating Confidentiality of Encrypted Search Systems: A Probabilistic Framework

We develop a probabilistic framework for quantifying the confidentiality of encrypted search systems based on the sampling distribution of a confidentiality statistic. Using the Bootstrap method with normal approximation, we efficiently estimate the risk of confidentiality breach, enabling proactive countermeasures. Our analysis shows how entropy of the query distribution relates to the adversary’s expected accuracy, providing theoretical grounding for resilience engineering approaches to encrypted search security.