Since the end of the Cold War, American presidents have chased a “reset” with Russia. Instead of repairing the relationship, those efforts have tended to produce a volatile cycle of false promises and strategic miscalculation. Today, President Trump risks repeating the pattern. His eagerness to engage and negotiate with Vladimir Putin echoes the approaches of the Clinton, Bush, and Obama administrations.

“Engagement and Enlargement” defined President Bill Clinton’s 1994 National Security Strategy. The collapse of the Soviet Union seemed to open a new era for U.S.–Russian cooperation, but it also left the fledgling Russian state exposed. Desperate for assistance to keep the economy afloat, President Boris Yeltsin pledged internal reform in exchange for U.S. aid.

When those reforms stalled and Yeltsin’s political will faltered, the Clinton team eased off, reluctant to press a fragile government. Rather than insist on a fuller democratic trajectory, the administration muted criticism of Yeltsin’s limited progress. The initial period of mutual optimism quickly soured: Russian opposition to U.S. intervention in Kosovo, NATO expansion, and the Second Chechen War strained ties by the end of Clinton’s second term.

At first, the George W. Bush administration seemed to absorb the lessons of Clinton’s Russia policy. Then, National Security Adviser Condoleezza Rice argued in a 2000 Foreign Affairs essay that Clinton’s embrace of Yeltsin had failed—support for Russian democratic and economic reform had little effect on Russia’s political development and induced U.S. concessions tailored to Yeltsin’s needs.

But the Sept. 11, 2001 attacks shifted Bush’s strategy. The 2002 National Security Strategy cast Russia, in a “hopeful transition” toward a “democratic future,” as a key asset in the war on terror. With that reframing came a familiar dynamic. Just as Clinton had counseled Yeltsin, Bush chose to treat Putin as the steward of a transforming Russia—famously claiming to have looked into Putin’s soul, then inviting him to the Texas ranch and to Camp David. (The optics are not far from Trump’s decision to host Putin in Alaska with a red-carpet welcome.) As with Clinton, however, Bush’s approach didn’t hold.

After Putin’s 2007 speech at the Munich Security Conference and Russia’s invasion of Georgia, the Obama administration rolled out a “reset” intended to repair a badly frayed relationship. On paper, the reset was pragmatic: use cooperation only to achieve concrete mutual interests, not to improve atmospherics for their own sake. Even so, President Barack Obama sought to capitalize on the early “honeymoon” that followed his and Dmitry Medvedev’s elections—famously asking for “space” with a promise of “flexibility” on key issues later. That bet proved short-sighted. As relations deteriorated near the end of Obama’s second term, many of the agreements and institutions built during the reset were left vulnerable to Russian pressure.

Trump appears poised to make the same mistake: personalizing his relationship with Putin and overestimating his ability to extract durable cooperation from Moscow. Rather than building a long-term Russia strategy, new presidents are often tempted by the apparent gains that come from acting quickly to “restore” relations. To be sure, periods of cooperation have produced arms-control deals and episodic counterterrorism support. But because these openings are short-lived, they do little to resolve the central problem of European security. When the window closes, Moscow exploits the renewed chill to test its neighbors’ defenses—as seen in the 2007 cyberattack on Estonia, the 2008 invasion of Georgia, and the 2014 invasion of Ukraine. Administrations may convince themselves that near-term wins outweigh the costs of sustained confrontation; what they miss is how those honeymoon-era agreements become exposed once the relationship snaps back to rivalry.

To avoid relapsing into this cycle, Trump needs to balance diplomacy with a clear-eyed view of Putin’s aims. Open channels will be necessary to end the war in Ukraine, but Washington cannot trade away core U.S. interests for the illusion of stability. Seizing on the optics of personal rapport amid persistent tensions is shortsighted, especially when today’s choices demand long-horizon solutions. Because Putin’s conception of Russian power fundamentally clashes with U.S. interests, any periodic stride in U.S.–Russia relations is likely to unravel unless it is grounded in hard limits, sustained deterrence, and a strategy that outlasts any single leader-to-leader moment.