Sources told CNN that United States officials have established a contingency plan for a potential second day of discussions between Trump and Kim depending on the direction of their planned meeting on June 12.
But Trump - for whom a major accomplishment would bolster his position ahead of midterm elections in November - baffled observers when he said he did not think he had to prepare "very much" for the summit.
Though it could mean many things, the relative speed of the reports about Singapore could be seen as a sign of confidence by the North that the summit will go well.
Kim and his delegation arrived aboard an Air China 747, according to Singapore's Straits Times.
Trump touched down in Singapore on Air Force One Sunday, where he was greeted by Singaporean Foreign Minister Vivian Balakrishnan and the U.S. Embassy's chargé d'affaires Stephanie Syptak-Ramnath. "It's North Korea", said one western tourist with a shrug.
A dictator who until March had not even visited his closest neighbour and ally China, now being treated not as an worldwide pariah but a global statesman on the same level as the U.S. president.
The talks will focus on reaching an agreement on the denuclearisation of North Korea in exchange for the easing of economic and diplomatic sanctions. A source cited by Reuters, however, said that Kim is tentatively scheduled to leave Singapore at 2:00 P.M. Tuesday, suggesting the meeting could be a short affair. At the G7 summit in Canada and in the hours afterward, Trump railed against trade practices that he described as unfair and said he'd given US representatives instructions to rescind an agreement to official communique that outlined a mutual plan to ensure "free, fair, and mutually beneficial trade".
"The fact that we have been chosen as the site of the meeting, we did not ask for it.it says something about Singapore relations with the parties. and our standing in the global community", he said, according to Channel News Asia.
"The summit will represent a major diplomatic win for Mr. Trump ahead of the USA midterm elections later this year".
Security for Kim Jong Un at his first meeting with Trump is expected to be ultra-tight, with measures likely surpassing those seen at the April 27 inter-Korean summit, experts and analysts say.
Balakrishnan had visited Washington earlier in the week and met with U.S. Secretary of State Mike Pompeo and U.S. National Security Adviser John Bolton.
"We continue to call on North Korea to completely, verifiably, and irreversibly dismantle all of its weapons of mass destruction (WMD) and ballistic missiles as well as its related programs and facilities", it said.
Kim smiled broadly Sunday evening as he met with Singapore Prime Minister Lee Hsien Loong. The high-anticipated talks had been put at risk, when, on May 24, Trump announced he was canceling the meeting with Kim over Pyongyang's hostile rhetoric.