The Chatham House Istanbul Roundtable was created in 2010, one year prior to the Arab Spring, to explore developments in the Middle East and North Africa (MENA) region. No one at that time could have anticipated the collapse of republican presidencies in Tunisia, Egypt, Yemen, and Libya; the civil war in Syria; the implosion of Iraq; or the rise of the Islamic State of Iraq and the Levant (ISIL). Today, the reality in the region is increasingly complex, messy, and unpredictable. This article presents a summary of the Chatham House’s fifth annual Istanbul Roundtable to examine the dynamic changes sweeping the MENA region, the implications of ISIL’s emergence in Syria and Iraq, and the long-term prospects for democracy and economic prosperity in the region.