A United States official said Monday that after a handshake scheduled for 9 am Tuesday, Trump and Kim will first meet one on one with translators in a session that could last up to two hours before they open the meeting to their respective advisers.
"Wide-ranging and profound views on the issue of establishing new DPRK-US relations, the issue of building a permanent and durable peace-keeping mechanism on the Korean Peninsula, the issue of actualizing the denuclearization of the Korean peninsula and other issues of mutual concern" will be discussed, state-run KCNA reported early Monday.
Many questions remain unanswered, however, including whether the North Koreans have robust enough communication systems to make sure no one panics and launches an attack, said Vipin Narang, an associate professor at the Massachusetts Institute of Technology's Security Studies Program. They believe Kim's latest engagement is aimed at getting the United States to ease the crippling sanctions that have squeezed the impoverished country.
Pompeo said Trump was "fully prepared" for the talks, and was optimistic that the outcome would be "successful", while warning that there was still "lots of work left to do".
Reunification, he said, would be impossible because four powers - the US, China, Russia and Japan - do not want to see a unified Korea.
Still, some experts say it's important that both leaders come into the meeting with clear, realistic goals. He told reporters in Quebec on Saturday that he'd know "in the first minute" whether he could get to a deal with Kim, repeating that he wouldn't waste his time - but suggested that the time he's invested in this initial engagement wasn't such a big deal.
The meeting lasted more than two hours and took place at the Ritz Carlton. That evening, he said in a tweet that "great progress" was already being made and that denuclearization - "not just a freeze" - was on the table.
But just a year ago, Trump described the North Korean leader as "little rocket man", and warned of a USA military attack full of "fire and fury".
The other area was Sentosa Island, site of the Capella Hotel which will be the venue for the June 12 summit.
Still, even as he turned his attention to the summit, Trump continued his blistering attacks on Canadian Prime Minister Justin Trudeau Monday, saying "Fair Trade is now to be called Fool Trade if it is not Reciprocal".
But there are doubts denuclearisation of North Korea is achievable in the short term.
Trump has said he doesn't think he needs much preparation for this summit.
Though Trump has been criticized for his failure to demand more concessions from North Korea before agreeing to a face-to-face meeting, which experts say gives Kim the sort of legitimacy on the global stage he desires, downplaying expectations does two things.
Kim met with Singapore's Prime Minister Lee at his Istana residence after his arrival, in talks which North Korea's KCNA news agency said proceeded "in an amicable and friendly atmosphere".
Kim and his delegation arrived aboard an Air China 747, according to Singapore's Straits Times. There was also no sign of his sister, Kim Yo Jong, who has accompanied him to Singapore.
The North Korean leader has in recent months been trying to shift his image from reclusive tyrant to smiling statesman.
Officials who arrived with Trump include Pompeo, National Security Adviser John Bolton, White House Chief of Staff John Kelly and White House Press Secretary Sarah Sanders.