The ancient Greeks and Romans were fully aware of the necessity of obtaining, protecting and communicating military intelligence. The timely delivery of information often turned the tide of battle to advantage, and the lack of it to disadvantage and even disaster. The ancient Greek and Roman literature is replete with examples of intelligence gathering, analysis and communication. Intelligence failures are not ignored, but recorded and discussed. In this paper we examine the ancient primary sources to understand what role cryptography and steganography played in Ancient Greece and Rome. A brief discussion of ancient Greek and Roman intelligence techniques and some modern examples (drawn from secondary literature) of intelligence failures are included in the discussion. This serves to demonstrate that the ancient Greeks and Romans were sophisticated in their use of technology, and faced many of the same problems we face today. The question in this ongoing research project is then asked, is it possible to draw lessons that are applicable to modern intelligence and information warfare activities? It is concluded that of the incidents and technologies analysed, the failures are the result of non-technological factors, and that we can profit from a more detailed study of ancient primary sources.