New Tottenham midfielder Clint Dempsey needed only 36 seconds to put the Americans ahead, but Leeds midfielder Rodolph Austin equalised 20 minutes later with a fierce free-kick which deflected off defender Kyle Beckerman and beat Tim Howard.
Then, in the second half, Everton goalkeeper Howard was beaten by another free-kick, this time Luton Shelton the man on target.
United States coach Jurgen Klinsmann was disappointed with his side's performance.
"They were hungrier and more determined," the German said of the Jamaicans. "We have to fix some mistakes if we want to recover quickly."
The result lifted the Reggae Boyz to the top of the pool on seven points - two ahead of the Americans and Guatemala, which had to work hard to sink Antigua & Barbuda 3-1.
Peter Byers silenced the home crowd by putting the visitor ahead in the 38th minute, but Carlos Ruiz's second-half brace turned the game on its head before substitute Dwight Pezzarossi sealed matters in stoppage time.
The result left Antigua & Barbuda bottom of the group on one point ahead of Wednesday's fixtures, in which it faces Guatemala and the USA hosts Jamaica.
In Group B, Mexico maintained its perfect record with a straightforward 2-0 victory over Costa Rica in San Jose.
Carlos Salcido volleyed home the opener two minutes before the interval, after being set up by Javier Hernandez, and Jesus Zavala converted a corner to double the Mexicans' advantage seven minutes into the second half.
"It's always very complicated to play in San Jose, but we did it well and we could even have won by a bigger margin," Mexico coach Jose Manuel De La Torre said.
"We have to think and plan every game like it was our last. We have not achieved our main target yet."
In the pool's other game, El Salvador could only manage a 2-2 home draw against Guyana. Isidro Gutierrez and Osael Romero netted the goals for the host, with Treyon Bobb twice on target for the visitor.
Mexico's win moved it to the brink of clinching a place in the final qualifying round. It advanced to nine points - five ahead Costa Rica and eight more than the Salvadorians.
On Wednesday, Mexico faces Costa Rica and Guyana will host El Salvador.
Finally, in Toronto, Canada beat Panama 1-0 thanks to a 77th-minute strike by veteran Dwayne De Rosario - and overtook the Canaleros at the Group C summit.
Stephen Hart's Canadians progressed to seven points - one more than Panama - ahead of Wednesday's return clash between the nations.
In the other pool match, goals from Jerry Bengston, Victor Bernardez and Marvin Chavez saw Honduras stroll to a 3-0 win over Cuba in Havana. The teams will meet again in San Pedro Sula on Wednesday.