In April of 2005, multiple errors in the navigation software code that were overlooked during rushed testing phases caused the Demonstration of Autonomous Rendezvous Technology (DART) spacecraft to crash into the target satellite with which it was attempting to rendezvous. It was operating entirely on pre-programmed software with no real-time human intervention. The same navigational errors resulted in the premature expenditure of fuel and early end to the mission without the $110 million program having completed any of its close-range technical objectives. The DART team did not adequately validate flight critical software requirements, including late changes to the code that proved critical in this mishap. The program used an inappropriate heritage software platform and a team that lacked the levels of experience needed to operate with such little oversight. As NASA continues to push the envelope with newer cutting edge autonomous technologies, we must keep in mind the basic principles that make any technology program successful. Validation, verification and peer review cannot be sacrificed for schedule, and we must fully utilize our past experiences and expertise on current and new projects. We must be careful to ensure that we are not simply automating failure.