News thattook the international community by surprise, but national security experts say a successful outcome of the talks is in everyone's interest.
"Because President Trump has already said 'yes' to this meeting, if it happens, this meeting is too big to fail," said Jung Pak, a senior fellow at the Brookings Institution.
Pak said the larger-than-life personalities of the two leaders could be an impediment during discussions, saying a possible inability to "get along" is a risk to dialogue.
"If you have two confident leaders coming to the table demanding things of each other, they're not going to get along. But the other side is that, if they do get along and somehow [Mr. Trump] thinks that he's getting a win from Kim Jong Un -- and that we have this convergence of a U.S. president who is suspicious of alliances in general -- that he might be willing to trade away the alliance for some sort of win for the United States, such as no ICBMs, for example," explained Park.
Michael Morell, former acting director of the CIA and a CBS News senior national security contributor, agreed, saying the two leaders believe they are coming to the table from a position of strength and that both sides have high expectations of what they want to accomplish by meeting.
"North Korea in general and Kim Jong Un in particular put a very high value on being seen as meeting with the president of the United States. It gives him legitimacy both at home and abroad. It is very important to him. He will get that if this happens," said Morell.
Morell noted that the U.S. "could have gotten more" from the North Koreans beyond a promised short-term freeze in its nuclear testings. He said the best outcome of a meeting would be if "they meet and they set agree on a set of principles by which negotiations would continue at a lower level."
"One of the worst outcomes is a breakdown, is that the meeting doesn't go well and there's sniping at each other afterwards," Morell continued. "Because, where do you go from there, right? That's the danger here. The other worst outcome is if we take the pressure off in some way, that if we give some sort of sanctions relief for something not very significant."
While Mr. Trump appears to be hopeful for the North Koreans following through on their promises, Pak says the sudden silence from the regime could be Kim's "dangling of the possibility of willingness" to meet.
"We haven't heard anything from North Korea that these talks have actually been offered or that any concessions or so-called concessions have been offered," Pak said. "All of this is coming secondhand from the South Koreans who have an interest in making sure that the North Korea and U.S. talks happen."
She added, "North Korea is keeping mum and I'm not surprised about that, given that gives them maximum flexibility on their next moves. And I'm sure that Kim is monitoring all the discussions and debate going on in Washington about whether or not President Trump should happen have accepted this offer."
Park said she "wouldn't be surprised if we see some policy dysfunction from North Korea or a delayed reaction or response from North Korea as a result."