This story has been updated.

Following criticism for his "low energy" style and failure to attack Donald Trump more aggressively, Jeb Bush's campaign unveiled a new Web video on Tuesday that raises doubts about the sincerity of the GOP front-runner's Republican bona fides -- and his cultural connection to residents of the first-in-the-nation caucus state, where Trump is on top and Bush is mired in the single digits.

The video begins with an interview where Trump offers a geographic explanation for his political views. "I've lived in New York City and Manhattan all my life, ok, so my views are a little bit different than if I lived in Iowa," he says in the clip.

The video goes on to show Trump in a series of television interviews praising Democratic front-runner Hillary Rodham Clinton, and includes mentions of the mogul's previous support for higher taxes on wealthy Americans, a single-payer health-care system and the 2009 economic stimulus program.

A Jeb Bush ad shows Donald Trump in a series of television interviews. (Jeb Bush)

Bush tweeted out the video on Tuesday morning, a signal that the candidate is now more willing to attack the businessman. In recent days, he appeared to be attacking Trump reluctantly, and only at the prompting of supporters.

The new video comes a day after Donald Trump used a short video posted on Instagram to attack Bush for calling illegal immigration an "act of love." The video's chilling imagery recalled the infamous "Willie Horton" ad run against 1988 Democratic presidential candidate Michael Dukakis.