Most email users are still using the same email address set up fifteen years ago. Attained from their Internet service provider or having a free email account provided by Yahoo, Gmail or their college. The difference between most people is, secure and unsafe email can be found to be innocent. After all, we have nothing to hide, no illegal activities or anything dangerous. Google, Yahoo, and other webmail service providers use SSL/TLS or alternative methods to encrypt email communications in transit. S/MIME offers encryption, validation, message reliability and non-repudiation. We propose a novel proxy-re-encryption based webmail and file sharing system (PREWM). The PREWM server framework for a provable secure way for users to register the sharing of messages and content with a third-party cloud-based webmail system. In such a way, an intended receiver that neither has a cloud-based webmail provider or a proxy web server will be able to see the contents stored in the Webmail server. We make use of a cryptographic primitive called proxy re-encryption (PRE) to realize end-to-end privacy while sharing the contents of collaborative development. Also, we present the initial architecture and implementation in an Internet setting. We present the system architecture and its implementation. This paper will serve as a prototype for building next-generation webmail that can be adapted to any operating system.