In this paper, we present a framework for achieving anonymity and trust, two seemingly contradictory properties, in distributed systems. Our approach builds on webs of trust, a well-established and widely deployed decentralized infrastructure for establishing the authenticity of the binding between public keys and users, and more generally, trust relationships among users. We introduce the concept of anonymous webs of trust – an extension of webs of trust where users can authenticate messages and determine each other’s trust level without compromising their anonymity. Our framework comprises novel cryptographic protocols based on zero-knowledge proofs for achieving anonymity in webs of trust and a prototype implementation based on GnuPG. We conduct an automated analysis to formally verify the security of our protocol and an experimental evaluation to demonstrate the effectiveness of our approach. Categories and Subject Descriptors: C.2.0 [General]: Security and Protection General...