Before devising how to break through to Russians, Washington should pause a moment to understand what it’s done wrong so far. One of President Obama’s strongest signals to the Kremlin throughout the Ukraine crisis has been America’s second round of sanctions, which targeted 16 of Putin’s closest political allies. The list includes four members of Putin’s so-called “inner circle”—an attempt to sow dissension within the Kremlin’s ranks, and a symbolic gesture implying that Putin’s power is owed to illegitimate business ties.

Putin’s dubious connections to these men—billionaires like Gennady Timchenko and the Rotenberg brothers—could be politically explosive. Thanks in no small part to Putin’s own ceaseless vilification of 1990s-era oligarchs, any relationship with big business has the potential to ruin a Russian politician. As columnist Oleg Kashin observes, rumors about dirty dealings with men like Timchenko and the Rotenbergs have mushroomed into the Kremlin’s biggest liability today. This is why opposition leader Alexey Navalny has focused his anti-corruption activism on precisely this pressure point.

But when the U.S. published its sanctions against Russian elites, it bungled the timing: the list was made public just hours after a rare and widely read op-ed in the New York Times by none other than Alexei Navalny. That article, “How to Punish Putin,” named all four of the men the Treasury Department identified as “members of the Inner Circle” and called for the U.S. to sanction them. Navalny’s supporters joked about the coincidence, but the political fallout was terrible for the Russian opposition. Already considered a fifth column inside Russia, it looked to really be working hand in glove with the American government.

The White House might be forgiven for the unfortunate timing, except this isn’t the first time Washington has displayed this kind of cluelessness. Almost five years ago, Obama scaled back the deployment of U.S. missile-defense installations in Eastern Europe, paving the way for the New Start Treaty and a brief thaw in relations with the Kremlin. It was a huge concession to Moscow at the expense of the Poles and, making matters worse, the announcement came on September 17, 2009, the seventieth anniversary of the Soviet invasion of Poland. This inattention to detail only exacerbated the sense that the U.S. was throwing Poland under the bus for the sake of its relationship with Russia, which had already been cultivating doubts about America’s commitment to Eastern Europe. (Less than three months later, Poland's prime minister would say of America and its “reset” with Russia, “I can only have the satisfaction of being the first prime minister over the past fifteen years who isn’t so enchanted with our ally.”)