Osie Greenway started his freelance career in 2012 covering the Syrian refugee crisis spilling over the Jordanian border and the economic unrest in the country that was expressed in riots and protests. From Jordan he moved to Beirut, Lebanon and continued covering the plight of the Syrian refugees and sectarian clashes linked to the Syrian conflict in 2013-2014. Late 2014 he arrived in northern Iraq to cover the war erupting as the group known as ISIL stormed military bases and captured the city of Mosul from the Iraqi Army. There he stayed until the summer of 2015 documenting the ongoing war between the Kurdish Peshmerga and the Islamic State group. He is currently based in Iraq covering the offensive to retake the city of Mosul. He is a Frontline Freelance Registered member and a RISC XII alumni and founder of the War Zone Freelance project.

He is currently based in Iraq where he works as a freelance photographer covering the Mosul Offensive and director of the War Zone Freelance project.