Monkeysphere provides a robust, decentralized, out-of-band Public Key Infrastructure (PKI) based on OpenPGP's Web of Trust. It is intended to support any protocol which needs public-key authentication or binding between public keys and real-world entities. Current implementations include mutual authentication (both server and client) for SSH and authentication of servers for HTTPS. The technique is resistant to X.509's inherent single-issuer policy bias, allows use of a single key for a host offering multiple services, and handles initial contact, re-keying, and revocation better than OpenSSH's traditional key continuity management (KCM) scheme. It also requires no changes to on-the-wire protocols, and is transparently interoperable with existing tools, so the migration path to the new PKI is smooth (and encouraged). Discussion will include the merits and drawbacks of the Monkeysphere, as well as its relationship to in-band measures (such as the Server Name Indication (SNI) TLS extension and the subjectAltName (sAN) extended attribute for X.509v3 certificates) which provide some pieces of similar functionality.