Abstract: Much attention is paid in the management literature as to why software-intensive command and control projects fail during the acquisition process. But many do enter service successfully only to fail during operational use, sometimes catastrophically. The author suggests that quite fundamental differences between the natural characteristics of command and the virtual rule-bound properties of software are a major cause of these catastrophic incidents. Some well-publicised examples are used to illustrate the extent of the breakdown between command and automation that can occur in real operations. Since in the future, it is likely that military operations will be more complex and unpredictable than those of the past, the author suggests that Military Users should be increasingly on guard to prevent technological hubris from constraining the operational flexibility of future systems. It is suggested that Military Users should take an active leadership role alongside Industry in the procurement process to ensure the 'Risky Dualism' between command and automation is addressed during system design, and not when it is too late.