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The Islamic State’s prolific use of chemical weapons in Syria and Iraq stunned the world, as it was the first such non-state actor to do so. Prior to the Islamic State, only other non-state actors to have successfully deployed chemical weapons were the Tamil Tigers (once) and Aum Shinrikyo (a total of 10 attacks), but neither one of them carried out chemical attacks as large scale as the Islamic State – both in magnitude of attacks and in frequency. For the state actors, only four states have deployed chemical weapons in large scale since the latter half of the twentieth century (the number of states increase if one includes state-sponsored assassinations). One of the four states was the United States, who deployed napalm and Agent Orange during the Vietnam War. The other three states were Egypt, Iraq, and Syria who deployed chemical weapons such as mustard gas, phosgene, tabun, and sarin specifically against civilians and “rebel” fighters during intra- and inter-state conflicts. This paper seeks to compare and contrast the conditions under which the Islamic State deployed chemical weapons with those Egypt, Iraq, and Syria were under when they deployed chemical weapons during their respective conflicts to gain deeper insights into the Islamic States’ decision to deploy, almost routinely, chemical weapons against targets in Syria and Iraq.