Although video releases have been central to the Islamic State’s efforts to represent itself to its audiences, an extensive quantitative and qualitative study of these sources over a longer period of time is still lacking. This paper therefore provides an overview and analysis of the entire corpus of official videos released by the Islamic State between 1 July 2015 and 30 June 2018. It particularly focuses on how the Islamic State’s decline in Iraq and Syria during this period is reflected in its video output and how the group has responded to its setbacks. The paper demonstrates a strong correlation between the group’s mounting troubles and its video production: the numbers of videos decreased dramatically and their content reflects the Islamic State’s (re)transformation from a territory-based ‘state’ to an insurgent group relying on guerrilla tactics and terrorist attacks. Nevertheless, this paper argues that the Islamic State’s multi-faceted response to its setbacks might ensure the groups’ appeal to its target audience in the years to come.