The All Whites didn't lack for enterprise going forward, but occasionally did lack a clinical edge in and around the penalty area.
The hosts should have been awarded a penalty in the game's nascent stages, before falling behind to a cross-cum-shot shortly before the break.
Tony Lochhead was exposed to the speedy Jamaicans for two second half goals, sandwiched around Chris Wood's second goal for his country, and Chris Killen grabbed a late consolation.
The All Whites may not have to wait long for revenge. If New Zealand win advance through Oceania qualifying, will play the fourth-ranked side in Concacaf in a two-legged play-off for a spot at the 2014 World Cup, a position presently occupied by Jamaica.
New Zealand will want to tidy up some rough edges before then but, in truth, they were always up against it tonight.
Jamaica, ranked at 50, 70 places higher than their hosts, have played three games in nine days while the All Whites only had a light training run last night with their full squad.
The game sparked to life in the sixth minute, with Tahitian referee Norbert Hauata drawing the ire of the home crowd by turning down what looked like a sure penalty for the All Whites after the lively Marco Rojas was brought down by Jamaican keeper Jacomeno Barrett.
The game then settled into a probing period, with the All Whites' reunited World Cup back three were largely untroubled in defence for most of the half, while the young attacking trio of Chris Wood, Kosta Barbarouses and Rojas were impressing up front with an interchangeable pass-and-move game.
But it was a more direct approach which brought the All Whites' first shot on target, with Ryan Nelsen going agonisingly close to repeating his goalscoring heroics of 10 years ago.
At the same end from which he sent New Zealand to the 2002 Confederation's Cup by volleying the only goal against Australia, the All Whites captain was denied by Barrett after another set piece fell to his feet.
The All Whites continued to press but it was Jamaica who took a 38th minute lead in fortuitous circumstances, with fullback Xavian Virgo's attempted cross floating over the head of a stranded Mark Paston and in off the far post.
The visitors took the advantage to the break before doubling their lead eight minutes into the second half, with Lochhead being exposed on his inside and Tramaine Stewart finishing with ease under Paston.
But the All Whites immediately hit back through Wood, after the big striker combined beautifully with Rojas to carve through the middle of the Jamaican defence. Rojas eventually laid off the ball to Wood just inside the area and the Bristol City striker finished with aplomb for his second international goal.
Lochhead was again beaten for pace as the Jamaicans appeared to make the game safe through a breakaway goal from Navian Boyd, before substitute Chris Killen added some intrigue to the closing stages by heading in Leo Bertos' corner five minutes from time.
Tommy Smith almost capped a standout display by nearly notching a stoppage-time equaliser but the Ipswich defender's header sailed agonisingly over the bar.
New Zealand 2 (Wood 54, Killen 89)
Jamaica 3 (Virgo 38, Stewart 53, Boyd 77)
HT: 0-1
