In the final days before the invasion of Ukraine, Russia’s security service began sending cryptic instructions to informants in Kyiv. Pack up and get out of the capital, the Kremlin collaborators were told, but leave behind the keys to your homes.
The directions came from senior officers in a unit of Russia’s Federal Security Service (FSB) with a prosaic name — the Department of Operational Information — but an ominous assignment: ensure the decapitation of the Ukrainian government and oversee the installation of a pro-Russian regime.
The messages were a measure of the confidence in that audacious plan. So certain were FSB operatives that they would soon control the levers of power in Kyiv, according to Ukrainian and Western security officials, that they spent the waning days before the war arranging safe houses or accommodations in informants’ apartments and other locations for the planned influx of personnel.
“Have a successful trip!” one FSB officer told another who was being sent to oversee the expected occupation, according to intercepted communications. There is no indication that the recipient ever made it to the capital, as the FSB’s plans collapsed amid the retreat of Russian forces in the early months of the war.
The communications exposing these preparations are part of a larger trove of sensitive materials obtained by Ukrainian and other security services and reviewed by The Washington Post. They offer rare insight into the activities of the FSB — a sprawling service that bears enormous responsibility for the failed Russian war plan and the hubris that propelled it.
An agency whose domain includes internal security in Russia as well as espionage in the former Soviet states, the FSB has spent decades spying on Ukraine, attempting to co-opt its institutions, paying off officials and working to impede any perceived drift toward the West. No aspect of the FSB’s intelligence mission outside Russia was more important than burrowing into all levels of Ukrainian society.
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And yet, the agency failed to incapacitate Ukraine’s government, foment any semblance of a pro-Russian groundswell or interrupt President Volodymyr Zelensky’s hold on power. Its analysts either did not fathom how forcefully Ukraine would respond, Ukrainian and Western officials said, or did understand but couldn’t or wouldn’t convey such sober assessments to Russian President Vladimir Putin.
[Hubris and isolation led Vladimir Putin to misjudge Ukraine]
The humiliations of Russia’s military have largely overshadowed the failures of the FSB and other intelligence agencies. But in some ways, these have been even more incomprehensible and consequential, officials said, underpinning nearly every Kremlin war decision.
“The Russians were wrong by a mile,” said a senior U.S. official with regular access to classified intelligence on Russia and its security services. “They set up an entire war effort to seize strategic objectives that were beyond their means,” the official said. “Russia’s mistake was really fundamental and strategic.”
Ukraine’s security services have an interest in discrediting Russia’s spy agencies, but key details from the trove were corroborated by officials in Western governments.
The files show that the FSB unit responsible for Ukraine surged in size in the months leading up to the war and was counting on support from a vast network of paid agents in Ukraine’s security apparatus. Some complied and sabotaged Ukraine’s defenses, officials said, while others appear to have pocketed their FSB payments but balked at doing the Kremlin’s bidding when the fighting started.
There are records that add to the mystery of Russian miscalculations. Extensive polls conducted for the FSB show that large segments of Ukraine’s population were prepared to resist Russian encroachment, and that any expectation that Russian forces would be greeted as liberators was unfounded. Even so, officials said, the FSB continued to feed the Kremlin rosy assessments that Ukraine’s masses would welcome the arrival of Russia’s military and the restoration of Moscow-friendly rule.
“There was plenty of wishful thinking in the GRU and the military, but it started with the FSB,” said a senior Western security official, using the GRU abbreviation for Russia’s main military intelligence agency. “The sense that there would be flowers strewn in their path — that was an FSB exercise.” He and other security officials in Ukraine, the United States and Europe spoke on the condition of anonymity to discuss sensitive intelligence.
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Adhering to these erroneous assumptions, officials said, the FSB championed a war plan premised on the idea that a lightning assault on Kyiv would topple the government in a matter of days. Zelensky would be dead, captured or in exile, creating a political vacuum for FSB agents to fill.
Instead, FSB operatives who at one point had reached the outskirts of Kyiv had to retreat alongside Russian forces, Ukrainian security officials said. Rather than presiding over the formation of a new government in Kyiv, officials said, the FSB now faces difficult questions in Moscow about what its long history of operations against Ukraine — and the large sums that financed them — accomplished.
The FSB did not respond to requests for comment.
The FSB’s plans and the efforts of Ukraine’s security agencies to thwart them — with backing from the CIA, Britain’s MI6 and other Western intelligence services — are part of a shadow war that has played out in parallel to Russia’s military campaign. It is a conflict that was underway long before the Feb. 24 invasion, and its battle lines are blurred by the tangled, overlapping histories of Russian services and Ukrainian counterparts that began as offspring of the Soviet-era KGB.
Six months into the war, neither side appears to have a clear upper hand.
The directions came from senior officers in a unit of Russia’s Federal Security Service (FSB) with a prosaic name — the Department of Operational Information — but an ominous assignment: ensure the decapitation of the Ukrainian government and oversee the installation of a pro-Russian regime.
The messages were a measure of the confidence in that audacious plan. So certain were FSB operatives that they would soon control the levers of power in Kyiv, according to Ukrainian and Western security officials, that they spent the waning days before the war arranging safe houses or accommodations in informants’ apartments and other locations for the planned influx of personnel.
“Have a successful trip!” one FSB officer told another who was being sent to oversee the expected occupation, according to intercepted communications. There is no indication that the recipient ever made it to the capital, as the FSB’s plans collapsed amid the retreat of Russian forces in the early months of the war.
The communications exposing these preparations are part of a larger trove of sensitive materials obtained by Ukrainian and other security services and reviewed by The Washington Post. They offer rare insight into the activities of the FSB — a sprawling service that bears enormous responsibility for the failed Russian war plan and the hubris that propelled it.
An agency whose domain includes internal security in Russia as well as espionage in the former Soviet states, the FSB has spent decades spying on Ukraine, attempting to co-opt its institutions, paying off officials and working to impede any perceived drift toward the West. No aspect of the FSB’s intelligence mission outside Russia was more important than burrowing into all levels of Ukrainian society.
Story continues below advertisement
And yet, the agency failed to incapacitate Ukraine’s government, foment any semblance of a pro-Russian groundswell or interrupt President Volodymyr Zelensky’s hold on power. Its analysts either did not fathom how forcefully Ukraine would respond, Ukrainian and Western officials said, or did understand but couldn’t or wouldn’t convey such sober assessments to Russian President Vladimir Putin.
[Hubris and isolation led Vladimir Putin to misjudge Ukraine]
The humiliations of Russia’s military have largely overshadowed the failures of the FSB and other intelligence agencies. But in some ways, these have been even more incomprehensible and consequential, officials said, underpinning nearly every Kremlin war decision.
“The Russians were wrong by a mile,” said a senior U.S. official with regular access to classified intelligence on Russia and its security services. “They set up an entire war effort to seize strategic objectives that were beyond their means,” the official said. “Russia’s mistake was really fundamental and strategic.”
Ukraine’s security services have an interest in discrediting Russia’s spy agencies, but key details from the trove were corroborated by officials in Western governments.
The files show that the FSB unit responsible for Ukraine surged in size in the months leading up to the war and was counting on support from a vast network of paid agents in Ukraine’s security apparatus. Some complied and sabotaged Ukraine’s defenses, officials said, while others appear to have pocketed their FSB payments but balked at doing the Kremlin’s bidding when the fighting started.
There are records that add to the mystery of Russian miscalculations. Extensive polls conducted for the FSB show that large segments of Ukraine’s population were prepared to resist Russian encroachment, and that any expectation that Russian forces would be greeted as liberators was unfounded. Even so, officials said, the FSB continued to feed the Kremlin rosy assessments that Ukraine’s masses would welcome the arrival of Russia’s military and the restoration of Moscow-friendly rule.
“There was plenty of wishful thinking in the GRU and the military, but it started with the FSB,” said a senior Western security official, using the GRU abbreviation for Russia’s main military intelligence agency. “The sense that there would be flowers strewn in their path — that was an FSB exercise.” He and other security officials in Ukraine, the United States and Europe spoke on the condition of anonymity to discuss sensitive intelligence.
Story continues below advertisement
Adhering to these erroneous assumptions, officials said, the FSB championed a war plan premised on the idea that a lightning assault on Kyiv would topple the government in a matter of days. Zelensky would be dead, captured or in exile, creating a political vacuum for FSB agents to fill.
Instead, FSB operatives who at one point had reached the outskirts of Kyiv had to retreat alongside Russian forces, Ukrainian security officials said. Rather than presiding over the formation of a new government in Kyiv, officials said, the FSB now faces difficult questions in Moscow about what its long history of operations against Ukraine — and the large sums that financed them — accomplished.
The FSB did not respond to requests for comment.
The FSB’s plans and the efforts of Ukraine’s security agencies to thwart them — with backing from the CIA, Britain’s MI6 and other Western intelligence services — are part of a shadow war that has played out in parallel to Russia’s military campaign. It is a conflict that was underway long before the Feb. 24 invasion, and its battle lines are blurred by the tangled, overlapping histories of Russian services and Ukrainian counterparts that began as offspring of the Soviet-era KGB.
Six months into the war, neither side appears to have a clear upper hand.
