As part of his general election strategy against John McCain, the presumptive Republican nominee, the Democratic presidential candidate is painstakingly courting those constituencies who have thus far remained largely resistant to his charms.
After his appearance before the B'nai Torah Congregation in Boca Raton, centre of Florida's influential Jewish community, Mr Obama travelled to Miami today (Fri) to address the Cuban American National Foundation, which is wary of his promise to end the ban on Americans travelling to Cuba.
Over the next few days, Mr Obama is increasingly concentrating on the general election, visiting swing states such as Nevada, New Mexico and Colorado.
Mr Obama appeared uncharacteristically nervous during the two-hour event in the synagogue, remarking after his opening address: "I suspect there may be people who are supporting other candidates in this audience and that's great - I want the toughest questions available."
Several of those gathered took up the challenge as he took question for well over an hour after he had proclaimed his "unshakable commitment to maintaining that bond between the United States and Israel and an unshakable commitment to Israel's security" and "deep affinity with the idea of social justice...embodied in the Jewish faith".
Right off the bat, he was asked about his name by a man who said he had a friend who would vote for him if he was called Barry instead of Barack. Mr Obama responded that it was true that many people would say he had "kind of a Muslim-sounding name and we don't know what's going on here".
He said that voters "shouldn't worry about the name because my understanding is in Hebrew it actually means lightning", adding: "You've had a prime minister named Barack [Ehud Barak] in Israel. It should be pretty familiar to this audience."
He also noted that "Barack" shared a root with the Hebrew word "baruch" or blessed.
Another questioner rattled off a long list of associations with supporters of the Palestinian cause, including Rashid Khalidi, an academic at Columbia University and named Jewish victims of terrorism before asking Mr Obama for a list of Jews who could vouch for him.
Mr Obama was irked by the question, responding: "I have to be very cautious about this," Mr. Obama said, "because you remember the old stereotype, 'I'm not prejudiced, some of my best friends are Jewish,' right? 'I'm not prejudiced, some of my best friends are black.' " But he duly listed a number of supporters, university professors and political advisers who were Jewish and strong supporters of Israel.
Outside the synagogue, there was a vociferous group of Jewish protesters, several of whom said they supported Mr McCain. "You are what your friends are and the company you keep is how I judge you," said Eli Albert, 17.
"Two friends he's had for 20 years have been the Reverend Jeremiah Wright and also Louis Farrakhan. Both of those have clearly stated they're anti-Israel and I can't stand for that. Israel is where my heart is."
Mr Obama recently cut tied with Mr Wright, his former minister, and he has never been a friend of Mr Farrakhan, though the controversial leader of the Nation of Islam has endorsed his candidacy.
Inside the synagogue, Mr Obama urged the congregation to keep an open mind. "We've got to be careful about guilt by association. The tradition of the Jewish people is to judge me by what I say and what I've done."
Exit polls have shown that Mr Obama's Democratic rival Hillary Clinton beat him convincingly among Jewish voters. But the Illinois senator's aides take comfort in other polls that show he leads Mr McCain among Jews - who tened to vote Democratic - by two to one.
"A lot of it is to do with a lack of familiarity and in politics people like to play on fears," said David Axelrod, Mr Obama's chief strategists, who is Jewish and was sporting a badge that said "Obama '08" in Hebrew.
"But I think the more the community has the opportunity to see him, to hear him, to understand where he comes from, that will dissipate."
Clarifying a comment last year that he would meet President Ahmadinejad of Iran "without preconditions", Mr Axelrod said: "His point is that if you can advance the cause of this country and the cause of peace by sitting down then he would do that."
But he added that "being willing" to meet Mr Ahmadinejad, who denies the Holocaust and wants to destroy Israel, did that mean that "he will".
Mr Obama said that he felt pained by tensions between the black and Jewish communities. "Don't judge me because I've got a funny name," he said in conclusion. "Don't judge me because I'm African-American. It's time for us to get past this."