Alan P. Gross of Maryland recently had the rare experience of being thrown in jail for doing his job.

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On Dec. 4, Cuban authorities arrested the U.S. Agency for International Development (USAID) contractor at Havana's José Martí International Airport. President Raúl Castro has said that Gross was providing "sophisticated satellite communications equipment" to groups working for "the enemy" -- that is, the Americans. Cuban prosecutors have yet to file formal charges, but he could be accused of entering the country on a tourist visa while actually working for a foreign government to foment regime change. Gross remains in a maximum-security prison in Havana, and U.S. diplomats are working assiduously for his release.

The case is the latest bone of contention between the United States and Cuba. And it is pushing President Barack Obama's administration to make a decision it neglected in its first year: whether to continue former President George W. Bush's policies toward Cuba, or forge its own ones.

Gross worked for Development Alternatives Inc. (DAI), a USAID contractor. According to his employer, at the time of his arrest Gross was distributing "equipment such as cell phones and laptops" to a "religious and cultural group recognized by the Cuban government," later identified as Cuba's Jewish community. A U.S. official says that Gross was passing out laptop-sized devices with satellite links to the Internet. It was simple "humanitarian assistance," DAI says. And Gross's friends and co-workers have scoffed at the idea that he was a spy. "He's not James Bond; he's a development guy," one friend told Washington Jewish Week.

Unfortunately for Gross, however, the USAID program he worked for is explicitly engineered to oust the Castros. It derives from the 1996 Helms-Burton Act, which tried to bring down a weakened Cuba following the fall of the Soviet Union. The law listed conditions for Cuba to meet to achieve democratic legitimacy -- among them that Fidel and Raúl Castro leave the government. Its Section 109 authorizes assistance for "individuals and independent nongovernmental organizations to support democracy-building efforts" -- in other words, USAID's grantees and contractors. In 2004, the Bush administration made USAID's Cuba program part of its effort to "accelerate the demise of Castro's tyranny" and increased its funding dramatically.

It is little wonder, then, that the communists in Havana have seen the USAID program as part of a regime-change strategy. Cuba responded in 1999 with its own Law 88, criminalizing any connection with the USAID program. It provides a prison term of three to eight years for "distribution of financial, material, or other resources that come from the United States government, its agencies, subordinates, representatives, functionaries, or private entities."

This leaves USAID in an unusual position: operating an assistance program in Cuba with the absurd hope that the local government will not notice. Stranger still, the program is overt in the United States -- in 2006, there was an open call for proposals for "high tech communication devices to facilitate communications between activists on the island" -- and attempts to be covert in Cuba.

That might work -- and Gross might be a free man today -- were it not for the fact that Cuba has a world-class intelligence service. At the Havana airport, passengers and baggage are scanned entering Cuba. Carry a laptop, and you can expect to answer a few questions. Carry several, and you can count on being watched. If you visit the U.S. diplomatic mission, Cuban guards see you coming and going. If you go there to pick something up -- the State Department reports that in some months, up to 75 percent of shipments to that mission come from USAID's grantees -- then the mission's 250 Cuban employees, all of whom can be counted on to be informants or employees of Cuba's Interior Ministry, will see that too.

Foreigners who phone or visit dissidents can expect to be observed. Moreover, "dissidents" aren't always who they seem -- indeed, Cuba's Department of State Security (DSS) not only monitors anti-government activists, but also manufactures some. Agents pose as opponents of the regime and infiltrate opposition organizations. When 75 dissidents were jailed after lightning trials in 2003, the DSS happily unmasked 12 of its phony dissidents, publishing interviews and then a book about their undercover exploits.

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