Social media are becoming sites of information operations-activities that seek to undermine information systems and manipulate civic discourse [26,36,44,47]. Through a mixed methods approach, our research extends investigations of online activism to examine the “work” of online information operations conducted on Twitter. In particular, we analyze the English-language conversation surrounding the reemergence of Omran Daqneesh (the “Aleppo Boy”) on Syrian state television, almost a year after his family’s home was bombed in an airstrike conducted by the Syrian government. We uncover: a network of clustered users that contributes to a contested and politicized information space surrounding Omran’s story; the presence of undermining narratives that serve to disrupt the mainstream media’s narrative and confuse the audience; and the techniques used when promoting, defending, or undermining narratives. In the current climate of increasing polarization in online social spaces, this work contributes an improved understanding of information operations online and of the collaborations that take shape around and through them.