A system, apparatus, method, and machine readable medium are described for authentication with asymmetric cryptography. For example, a method in accordance with one embodiment comprises: generating a challenge at a server; encrypting the challenge at the server using a public encryption key; transmitting the encrypted challenge to a connected device having a first connection over a network with the server; providing the encrypted challenge from the connected device to a user device; decrypting the encrypted challenge using a private encryption key corresponding to the public encryption key to determine the challenge; converting the challenge to a converted challenge, the converted challenge having a different format than the original challenge; receiving the converted challenge at the connected device and providing the converted challenge from the connected device to the server; and validating the converted challenge at the server to authenticate the user.