This spring, after Bulgaria recalled Meglena Plugchieva from her ambassadorship in Berlin to clean up widespread corruption and misuse of European Union funds, she warned fellow ministers they must act to prevent the loss of massive funding from Brussels.

But Ms. Plugchieva also vowed to stand up to Western criticism that singles out her nation's ills. "Bulgaria is not the cradle of corruption," she said. "Germany also has its corruption-related scandals."

The "double standard" defense, though, wasn't enough to deter a stinging financial slap delivered last month by a European Commission angry after millions of euros in development assistance had been siphoned off and a string of high-profile corruption and murder investigations resulted in no convictions.

Bulgaria's case was putting the credibility of EU enlargement at stake: Brussels needed to send a message to those arguing against further expansion and to candidates banging on the door, including Croatia, Serbia, Albania, and Turkey. Just last month, EU officials warned Croatia that its failure to crack down on organized crime and corruption jeopardizes its chance to join the EU next year.

"Brussels needed to get serious, to show they're not just taking a country's word for fighting corruption," says Katinka Barysch, deputy director of the Center for European Reform in London. "If they can't do that with Bulgaria, how are you going to do that with the countries still queuing outside?"

In late November, Brussels slapped Sofia with an unprecedented penalty, withdrawing €220 million ($315 million) in development assistance – less than the initial threat of €500 million, but still a huge sum for the poorest EU member.

"This is not the most pleasant day of my life," said EU Enlargement Commissioner Olli Rehn, announcing the verdict. "As they say, the man's gotta do what the man's gotta do."

From the start, the accession of both Bulgaria and Romania to the EU raised eyebrows. During the postcommunist transition of the early 1990s, the Central European states of Poland, Hungary, and the Czech Republic swallowed bitter pills of democratic, free-market reforms. Romania and Bulgaria, meanwhile, started at a lower level of development and reforms were slowed by foot dragging, experts say.

As the economy worsened here, so, too, did corruption, says John Heck, who runs an EU-funded, anticorruption project in Sofia. The problems are ingrained deeply into modern Bulgarian society, he says, "Integrity – if you look in the Bulgarian dictionary, you won't find the term."

Although critics argued that Romania and Bulgaria would be allowed into the EU too soon, strategic benefits won out. Many Bulgarians were also eager to join, so Brussels dangled a carrot and stick to pressure authorities into complying with EU laws and standards. Still, enforcement lagged and corruption continued.

When Bulgaria and Romania were finally admitted to the EU in January 2007, they became the first to enter with strings attached: They were given several months to clean up their legal systems and to develop methods of tracking EU funding. Promises were made, but deadlines were missed, prompting a growing litany of threats from Brussels.

Romania soon launched several high-profile public prosecutions against corruption, but Bulgarian efforts struck EU officials as disingenuous, says Irina Novakova, Brussels correspondent for Bulgaria's leading newspaper, Dnevnik.

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