Even after the White House confirmed the summit, the run-up to it was not without roadblocks.
The meeting was kicking off at 9 a.m. local time Tuesday with a handshake between Trump and Kim.
The US was prepared to offer certainty to North Korea so they could be "comfortable that denuclearisation isn't something that ends badly for them".
Trump had called Kim "Little Rocket Man" and threatened to unleash "fire and fury like the world has never seen" on North Korea as it conducted several ballistic missile tests in defiance of worldwide warnings.
"I have little expectation from the summit", he said.
Top members of Trump's administration have said that the North Koreans wouldn't receive any benefits before taking steps to denuclearize - wary of falling into the same predicament that doomed previous agreements with the rogue regime. However, others reported that the Air China Boeing 747 took off before the leader's jet did by an hour or two as a security measure to avoid making his mode of transportation known.
While President Trump has spoken positively about the upcoming summit, he has been vague on details of what they might be able to actually achieve.
Many experts on North Korea, one of the most insular and unpredictable countries in the world, remain skeptical Kim will ever completely abandon nuclear weapons.
The cover of this week's edition of The Economis.
"Trump will hype this relentlessly, no matter what comes of it", tweeted Robert E Kelly, a political science professor at Pusan National University in South Korea who is town to comment on the summit for the BBC. "We must put the American worker first!"
Kim is due to meet Singapore Prime Minister Lee Hsien Loong later on Sunday, Singapore's ministry of foreign affairs said in a statement.
He has been involved in the country's relations with the US and South Korea for more than two decades.
Wagar told CNBC that until Trump, the recent USA position had been "we will have six-party talks that included Japan, Korea, China, the United States, and North Korea ..." In an op-ed, the Associated Press has expressed doubts that Kim "would fully relinquish his nuclear arsenal, which he may see as the guarantor of his survival". "Or we could have a failed summit that really takes us in the other direction".
So how should Trump communicate with Kim?
"The entire world is watching the historic summit between [North Korea] and the United States of America, and thanks to your honest efforts. we were able to complete the preparations for the historic summit", Kim reportedly told the Singaporean Prime Minister, Lee Hsien Loong, who he met in anticipation of the summit.
USA and North Korean officials met Monday at the Ritz Carlton in this island city-state to negotiate before the first sit-down between a United States president and a North Korean leader, which is meant to settle a standoff over Pyongyang's nuclear arsenal. Forging a peace treaty involving South Korea may be another topic of the Trump-Kim meeting. "If diplomacy does not move in the right direction".