President Barack Obama faces a tough challenge to his efforts to steer away from the policies of his predecessor in Iran. Obama’s diplomatic charm offensive in the Muslim world, and more specifically in relation to Iran, was hoped to breathe new life into the tortured relationship between the United States and Iran. This was a marked departure from the past. Regime change was out. Direct engagement was in. Obama refrained from repeating his predecessor’s threats against Iran, instead trying to find a way to influence the behavior of the ruling regime. In a clear effort to draw lessons from past mistakes, the Obama administration moved to address the emotive issues of respect and parity between the United States and Iran and endeavored to chart a path of noninterference. Despite this significant change in the U.S. position, little progress has been made in affecting the behavior of the Islamic regime. Iran continues to defy the international community with its nuclear program, insists on antagonizing Israel, supports Hizbullah, and dismisses international efforts to bring peace to the protracted Palestinian-Israeli dispute. In short, Iran revels in its pariah status. As a result, pressure has been mounting on President Obama to reconsider his policy of engagement and revert back to the pattern of punishment.