A sender driven certificate enrollment system and methods of its use are provided, in which a sender controls the generation of a digital certificate that is used to encrypt and send a document to a recipient in a secure manner. The sender compares previously stored recipient information to gathered information from the recipient. If the information matches, the sender transfers key generation software to the recipient, which produces the digital certificate, comprising a public and private key pair. The sender can then use the public key to encrypt and send the document to the recipient, wherein the recipient can use the matching private key to decrypt the document.