This paper draws on almost two decades of US foreign policy documents on political Islam and relations with the Muslim world as well as interviews conducted with key representatives of Turkey's AKP, Malaysia's PKR, and Indonesia's PKS. It argues that both political Islam and US foreign policy have matured over time. The Obama administration has adopted a more accommodationist posture towards the development of Islamic democracy, which allows second generation Islamist parties the space to evolve and establish a more mature Islamic democracy. Simultaneously, the moderation and focus on higher, universal objectives among second generation Islamist parties allows the Obama administration the opportunity to support the development of this version of Islamic democracy. The acceptance of Islamist parties by the US depends on three central factors: strategic value to the US; acceptance of the US economic and strategic goals; and lastly, commitment to democracy, pluralism, rule of law, and human rights. A number of Islamist parties are moving in the direction of fulfilling the third criteria; the second may be difficult, however, particularly in the context of such issues as the Israel-Palestine conflict; while the first criteria may often be a matter out of their control. However, this paper contends that the trend of political Islam and US foreign policy is towards mutual accommodation rather than further confrontation.