A network device receives TCP segments of a flow via a first SSL session and transmits TCP segments via a second SSL session. Once a TCP segment has been transmitted, the TCP payload need no longer be stored on the network device. Substantial memory resources are conserved, because the device may have to handle many retransmit TCP segments at a given time. If the device receives a retransmit segment, then the device regenerates the retransmit segment to be transmitted. A data structure of entries is stored, with each entry including a decrypt state and an encrypt state for an associated SSL byte position. The device uses the decrypt state to initialize a decrypt engine, decrypts an SSL payload of the retransmit TCP segment received, uses the encrypt state to initialize an encrypt engine, re-encrypts the SSL payload, and then incorporates the re-encrypted SSL payload into the regenerated retransmit TCP segment.