PGP is built upon a Distributed Web of Trust in which a user’s trustworthiness is established by others who can vouch through a digital signature for that user’s identity. Preventing its wholesale adoption are a number of inherent weaknesses to include (but not limited to) the following: 1) Trust Relationships are built on a subjective honor system, 2) Only first degree relationships can be fully trusted, 3) Levels of trust are difficult to quantify with actual values, and 4) Issues with the Web of Trust itself (Certification and Endorsement). Although the security that PGP provides is proven to be reliable, it has largely failed to garner large scale adoption. In this paper, we propose several novel contributions to address the aforementioned issues with PGP and associated Web of Trust. To address the subjectivity of the Web of Trust, we provide a new certificate format based on Bitcoin which allows a user to verify a PGP certificate using Bitcoin identity-verification transactions – forming first degree trust relationships that are tied to actual values (i.e., number of Bitcoins transferred during transaction). Secondly, we present the design of a novel Distributed PGP key server that leverages the Bitcoin transaction blockchain to store and retrieve Bitcoin-Based PGP certificates. Lastly, we provide a web prototype application that demonstrates several of these capabilities in an actual environment