During the first two decades following India’s independence, the CIA had a complex, and often conflicted relationship with the ruling Congress party and the Indian media. Despite public and private criticisms levelled at the Agency by Jawaharlal Nehru, a number of CIA covert operations in the subcontinent were undertaken with the full knowledge and support of India’s intelligence service and senior figures within the Congress Party: In Kerala, in the late 1950s, the CIA worked with the Congress Party to destabilise a democratically elected communist administration; following an abortive Tibetan uprising in 1959, India’s Intelligence Bureau chose to ‘look the other way’ as CIA aircraft transited through Indian airspace in support of Agency sponsored resistance operations in Chinese-controlled Tibet; and CIA operatives spirited the Dalai Lama out of Lhasa and into northern India. This chapter probes the genesis and evolution of the CIA’s relationship with India during the Agency’s so-called ‘golden age’ in the long 1950s, when a series of major US covert operations were conducted across the globe, in places such as the Congo, Guatemala, Iran, Indonesia, and Tibet.