One day you wake up and you have the sinking feeling that someone may be reading your e-mail correspondence. Your only recourse is to encrypt or hide your sensitive communications. This is a look at one web-based solution - CryptoMail - and how it deals with the problem of simplifying encrypted e-mail while maintaining a high level of confidentiality. A detailed analysis of the CryptoMail session establishment, message encryption, and data store model will be presented. Furthermore, a demonstration of the working system will be given and attendees may create accounts, ask questions, or comment on the system.