In the face of content takedown and account suspensions on the biggest social media platforms, terrorist groups and their supporters have resorted to the use of file-sharing sites to ensure stable access to their propaganda. Amongst those to have employed this strategy are supporters of the so-called Islamic State (IS). Yet, while studies have repeatedly highlighted the key role that file-sharing platforms play in the dissemination of IS propaganda, there has been little investigation of the strategic considerations that may influence the choice of file-sharing sites from the many available. To address this, this report uses data gathered from 13 public IS Telegram channels over a 45-day period in July – September 2021 to assess three possible strategic considerations: the features offered by different file-sharing sites (such as data storage capacity, maximum upload size, and password file protection); a platform’s enforcement activity; and the ability to generate large banks of URLs quickly and conveniently. Based on these findings, the report proposes a four-pronged strategy to combat the exploitation of file-sharing sites by supporters of IS and other terrorist groups: remove terrorist content at the point of upload; impede the automated generation and dissemination of banks of URLs; disrupt the posting of these URLs on other platforms; and redirect users to other content and support services.