Since the start of the Syrian civil war in 2011, the rich archaeological heritage of Syria and northern Iraq has faced severe threats, including looting, combat-related damage, and intentional demolition of monuments. However, the inaccessibility of the conflict zone to archaeologists or cultural heritage specialists has made it difficult to produce accurate damage assessments, impeding efforts to develop mitigation strategies and policies. This paper presents results of a project, undertaken in collaboration with the American Schools of Oriental Research (ASOR) and the US Department of State, to monitor damage to archaeological sites in Syria, northern Iraq, and southern Turkey using recent, high-resolution satellite imagery. Leveraging a large database of archaeological and heritage sites throughout the region, as well as access to continually updated satellite imagery from DigitalGlobe, this project has developed a flexible and efficient methodology to log observations of damage in a manner that facilitates spatial and temporal queries. With nearly 5000 sites carefully evaluated, analysis reveals unexpected patterns in the timing, severity, and location of damage, helping us to better understand the evolving cultural heritage crisis in Syria and Iraq. Results also offer a model for future remote sensing-based archaeological and heritage monitoring efforts in the Middle East and beyond.