This disclosure is directed to monitoring a crypto-partitioned, or cipher-text, wide-area network (WAN). A first computing device may be situated in a plain-text portion of a first enclave behind a first inline network encryptor (INE). A second device may be positioned in a plain-text portion of a second enclave behind a second INE. The two enclaves may be separated by a cipher-text WAN, over which the two enclaved may communicate. The first computing device may receive a data packet from the second computing device. The first computing device may then determine contents of a header of the data packet. The first computing device may, based at least in part on the contents of the header of the data packet, determine a status of the cipher-text WAN.