The increase of Israeli settlements has become "so substantial" it is inhibiting the possibility for an "effective, contiguous Palestinian state", President Barack Obama said in his final interview as president.
Speaking to CBS' 60 Minutes on Sunday, Obama dismissed the idea there was a "major rupture" in the relationship between the US and Israel after America's decision in December to abstain from a United Nations vote condemning Israeli settlements.
"Because of our investment in the region, and because we care so deeply about Israel, I think (the US) has a legitimate interest in saying to a friend, 'This is a problem'," Obama said.
The outgoing president reflected on his legacy and his biggest challenges during his eight years in office during the hour-long interview.
A number of his policies - from healthcare to his contentious relationship with Israel - could be short-lived as Donald Trump becomes the 45th president this week and vows to reverse some of those policies.
Trump has been vocal about his disapproval of many of Obama's policies, often voicing his disagreement or engaging in public disputes with the president on Twitter.
Over the holidays, Trump accused Obama of throwing up "inflammatory" roadblocks during the transition of power and his administration of treating Israel with "total disdain".
Obama acknowledged it had been an "unusual" transition, adding, "I suspect the president-elect would agree with that."
"We are moving into an era where a lot of people get their information through tweets and sound bites and some headline that comes over their phone," the president said.
"There's a power in that. There's also a danger - what generates a headline or stirs up a controversy and gets attention isn't the same as the process required to actually solve the problem."
He warned people not to "underestimate the guy" and urged congressional Republicans and Trump supporters around the country to be sure "that as we go forward, certain norms, certain institutional traditions don't get eroded, because there's a reason they're in place".
With that, he said he had been "disturbed" by intelligence reports over Russia hacking the US election.
"I have been concerned about the degree to which, in some circles, you've seen people suggest that Vladimir Putin has more credibility than the US government," he said.
Obama also reflected on his approach to the civil war in Syria as it approaches its sixth year, with hundreds of thousands dead and millions displaced around the world.
The president acknowledged that his "red line" declaration about the use of chemical weapons by Syrian President Bashar Assad's government was not in his 2012 speech and he did not have to use those words.
They later prompted harsh criticism, since the US did not follow through on the threat.
"I would have, I think, made a bigger mistake if I had said, 'Eh, chemical weapons. That doesn't really change my calculus'," he said.
"And regardless of how it ended up playing, I think, in the Beltway, what is true is Assad got rid of his chemical weapons."
