We revisit the problem of entity authentication in decentralized end-to-end encrypted email and secure messaging to propose a practical and self-sustaining cryptographic solution based on password-authenticated key exchange (PAKE). This not only allows users to authenticate each other via shared low-entropy secrets, e.g., memorable words, without a public key infrastructure or a trusted third party, but it also paves the way for automation and a series of cryptographic enhancements; improves security by minimizing the impact of human error and potentially improves usability. First, we study a few vulnerabilities in voice-based out-of-band authentication, in particular a combinatorial attack against lazy users, which we analyze in the context of a secure email solution. Next, we propose solving the problem of secure equality test using PAKE to achieve entity authentication and to establish a shared high-entropy secret key. Our solution lends itself to offline settings, compatible with the inherently asynchronous nature of email and modern messaging systems. The suggested approach enables enhancements in key management such as automated key renewal and future key pair authentications, multi-device synchronization, secure secret storage and retrieval, and the possibility of post-quantum security as well as facilitating forward secrecy and deniability in a primarily symmetric-key setting. We also discuss the use of auditable PAKEs for mitigating a class of online guess and abort attacks in authentication protocols.