Systems and methods for establishing secure remote connections to media devices establish a secure shell (SSH) connection between two machines which are located in two different private networks, such as between a remote debugging computer and a receiving device. The receiving device has a persistent outbound connection with a message server. The remote debugging computer connects to a relay manager and obtains a relay instance IP address and port. The relay manager then forwards the relay instance IP address and port to the receiving device via the message server. After receiving the connection request from the message server, the receiving device connects to the relay instance IP and port and waits for the input data. The remote debugging computer performs an SSH handshake and the receiving device directly authenticates the SSH connection.