The newly appointed US Ambassador to India Kenneth I. Juster recently elaborated that the US–India policy approach towards each other has been one of mutual respect, trust, acceptance, confidence, resilience and constancy (Juster, 2018). However, the reality of post-Cold War American engagement of India has been shadowed with both imperatives and irritants. The potential for defence trade and economic engagement in the aftermath of the Cold War triggered a major rethink by both. The American political will (especially Presidential) has been fundamental in acting as a catalyst at critical junctures. One juncture in the early 1990s was the push for a defence cooperation framework that continues to this day. The other major breakthrough that was achieved was the institutionalization of a dialogue architecture that would recast Indo-American relationships to a strategic partnership. End of Clinton’s term also provided breakthrough on two major irritants that had troubled the Indo-US relations namely nuclear non-proliferation and Pakistan. It also was apparent that Indian reciprocity to American overtures helped push the path of convergence and strategic alignment between the two. Bush administration built on this foundation but elevated the dialogue to a higher level. It was at this time that a formal strategic partnership was envisaged and a roadmap to achieve this was through the NSSP. Interestingly, the NSSP gave the US and India enough time to negotiate thorny areas such as non-proliferation. The signing of the Civil Nuclear Agreement and the defence agreement signalled the transformation underway in the relationship. During the discussions on the Civil Nuclear Deal, it was clear that the major gainer was India as there was an acceptance of it as a nuclear weapon state. The enormous political and presidential support to the Civil Nuclear Deal sent clear signals to the US Congress, which eventually signed the 123 Agreement in 2008. Thus, the era of bipartisan support for India in the US Congress was firmly established that hold till date. In addition, the de-hyphenation of India and Pakistan in US’ South Asia policy was clearly a major step in the evolution of Bush’s India policy. Obama years saw some changes and reversals in US policy. What was an initial coolness and mindset regarding India as part of security concern in the Af-Pak strategy became accommodative to Indian sensitivities and concerns. Underscoring India’s importance, Obama administration approached the frictions over the implementation of the Nuclear Deal through the first meeting of the SSD and Indian concerns over Af-Pak strategy through intricate diplomatic negotiations. In consequence, de-hyphenation with Pakistan continued, but after a disastrous meeting with the Chinese, ‘Pivot to Asia Strategy’ was put in place. The trigger that catalyzed US thinking at that point was the growing assertiveness of the Chinese and India’s strategic potential as a check against rising China. This reversal was noteworthy in itself, but it impacted even more strongly on the defence trade and security dialogue. India was first located as a net security provider in the Indian Ocean region, later as global power and finally as a major defence partner. The relationship was established as a defining partnership of the twenty-first century. The main catalyst was the China factor, but the lucrative Indian arms market came close second. India, in the US’ expectation, was not only to be a bulwark against China, but had the potential to develop as a close ally. Sceptics of Obama administration admitted that at the end, Obama had placed India–US strategic partnership on a firm footing based on the institutionalized negotiated approach and on shared strategic hopes and apprehensions. Under President Trump there has been a two-pronged approach towards this partnership so far. Given that this presidency was based on protectionism, alliance scepticism and emphatic personal leadership in a comparatively calmer geopolitical situation, India was seen both as an oasis of economic growth and stability. Early assessments from the administration reveal that India would continue to share US interests in South Asia and its relation with China will not impact India. The administration also recognizes that the relationship is expanding in a wide range of areas, including regional security, trade and economy as well as terrorism. The strategic embrace has remained anchored in expanding defence cooperation but several irritants on issues of trade, sanctions and relations with Russia and Iran are a part of the landscape of bilateral concerns. With US’ increasing focus on North Korea, recent developments have spelt turbulence in the relationship. Given this level of complexity in which there seem to be both convergences and divergences, the expectation is on the strong institutional architecture to continue to deliver benefits to the strategic partnership. As a caution, it would be wise not to allow a strategic drift either due to geopolitical compulsions elsewhere or dilution of political will to get in the way of the most promising partnership for both. Without political nurturing, structural compacts may in fact wither.