Every US incumbent dreads the “October surprise,” a convulsive international event just prior to elections. Syria’s violent takeover by anti-American Sunni extremists is the last thing that President Obama wants on the eve of US elections. The United States would be in a better position to steer Syria’s volatile transition by formalizing cooperation with Syrian freedom fighters, reaching out to in-country constituencies, and regionalizing cooperation through a contact group. Unlike its predecessor, the Obama administration should avoid decisions based on ideology or wishful thinking. A principled, proactive, and steely-eyed approach should guide US policy toward Syria.