There is a tendency in scholarly and strategic-policy fields to see the propaganda produced by groups like Islamic State and Al-Qaeda as historically unheralded. As evidence, slickly produced communiques and a penchant for using social media are typically highlighted. This narrow perspective, in placing the current phenomenon into an historical and thematic vacuum, infers that history has little to offer contemporary efforts to understand and confront extremist propaganda. This Research Paper explores the history of propaganda during conflict and draws out key lessons for improving counter-terrorism strategic communications. For millennia the evolution of propaganda strategies during conflict has been driven by three fundamental factors: (i.) developments in communication technology, (ii.) advancements in military technology and strategy, and (iii.) the shifting relationship between the political elite and the populace. This rich history offers vital lessons for contextualising and improving current (and future) efforts. Overall, history suggests that a strategic communications campaign during conflict is more likely to succeed if it based on a multifaceted approach characterised by the deployment of a diversity of messages that leverage a variety of target audience motivations, uses all pertinent means of communication (not just the latest), and synchronises this messaging with strategic-policy/politico-military actions. This Research Paper is a publication within ICCTâ€™s Counter-Terrorism Strategic Communications (CTSC) Project, which brings together experts from Europe, USA and Australia as well as researchers from the Middle East and South Asia. It was set up to tackle one of the most significant national and global security challenges facing the world today: how to understand and confront the propaganda messaging of violent extremists like al-Qaeda and the so-called Islamic State. Through empirical research, based largely on primary source materials and in-country fieldwork, the project aims to test assumptions and evaluate past campaigns in order to develop key principles and guidelines for counter-terrorism strategic communications efforts.