During the American Civil War, the Union made use of both tranposition and substitution ciphers for military messaging. The Confederacy had problems stringing anything together; the feds would have their attempts cracked within a day. Johnny Reb was terrible at cryptanalysis as well. They were so desperate, they took to publishing some enciphered Union messages in the local newspapers, hoping that anyone could help them figure out the codes.
(Pointed out by an online friend,) the Confederacy was the originator of the cryptoquip.