This paper presents SendIt, a novel approach aimed at enhancing the security and efficiency of file transfers over the Internet by combining Peer-to-Peer (P2P) technology with the web of trust model. Traditional methods of file transfer often compromise security by transmitting decryption keys and ciphers over the same channel, leading to vulnerabilities even among security specialists. SendIt seeks to address these issues by establishing a decentralized system where central services are only utilized when strictly necessary. By leveraging P2P communication, files are transferred directly between end-users, eliminating the need for intermediaries such as email exchange servers or cloud storage. This not only improves efficiency but also mitigates potential attacks by reducing the attack surface and minimizing the impact of the automatic spreading of malicious files. SendIt also implements a trust management system based on the web of trust model, allowing users to authenticate each other without relying on a central authority. Through reputation-based trust evaluation, users can make informed decisions about the level of trust associated with each identity. While SendIt demonstrates significant improvements in file transfer security and efficiency, further research is needed to address connectivity issues and optimize trust evaluation algorithms. Overall, SendIt presents a promising alternative to conventional file transfer methods, offering enhanced security and privacy for everyday users.