Abstract: Conventional SSL termination devices support secure connections only to a predetermined destination address. An SSL termination device accepts a plaintext connection and associate it to a secure connection to an arbitrary destination endpoint by intercepting a connection request from the local subnetwork, identifying the intended destination of the connection, and establishing a secure connection to the destination, bridges the local connection and the secure connection to provide a connection through the gateway device. The SSL termination device identifies an outgoing secure connection request from a client, and intercepts the connection request to identify the recipient destination. The SSL termination device establishes a secure connection using the identified destination, and associates the connections by mapping the intercepted connection to the recipient.