Social media and strategic communication sit at the heart of the war of ideas between the Islamic State in Iraq and the Levant (ISIL) and the West. The West is critically vulnerable to ISIL’s use of social media, shrewdly exploited in the recruitment of potential jihadists. This article argues that the Western world is losing the digital propaganda war waged by ISIL. At the strategic level, ISIL plans, synchronises and coordinates its social media efforts. Commanders provide operational updates and select content relevant to their strategic needs. From the battlefield, Western recruits tweet predominantly in their native language. Disseminators residing in the West and not officially aligned with ISIL, share and pass on ISIL’s propaganda. These proxy disseminators perform the vast majority of ISIL’s strategic narrative propagation. ISIL uses social media technologies that make the discovery and tracking of its recruitment propaganda difficult, exploiting the ‘deep web’ and ‘dark web’, severely hampering Western tracking agencies’ efforts to identify and isolate it. This article concludes that the West’s qualified moderate voice must be legitimised, encouraged and empowered to win the war of ideas. To do this the West must reform its strategic communication approach; it must comprehensively increase the volume of proactive participation in the ideological discourse conducted within the social media space.