A system, method and program product that evaluates trustworthiness of nodes participating in peer-to-peer transactions. A system is disclosed that includes: an input process for receiving a resource request from a consumer node; an identification analyzer that collects metadata associated with the consumer node; a transaction analyzer that extracts contextual data associated with the resource request; a matching engine that matches the consumer node with a set of provider nodes; and a contextual trust scoring engine that calculates a trust score for each of the consumer node and the set of provider nodes, wherein the trust score is based on the request, the metadata, and the contextual data.