President Donald Trump arrived in Singapore Monday morning ahead of the highly-anticipated summit with North Korean Dictator Kim Jong Un, which takes place on Tuesday, June 12.

But in spite of Trump's assurances that he is capable of making a deal with the reclusive North Korean leader, some officials close to the president are worried that his confidence may be his undoing.

According to the New York Times, sources who have been prepping Trump for tomorrow's historic meeting are concerned that the president's confidence has "allowed him to eschew detailed briefings on how Kim thinks about the world."

Last week, Trump said that he had been "preparing for this moment" his entire life and that he would know "within a minute" whether or not Kim is serious about potentially ending his nuclear weapons program.

When asked how he would know if Kim ends up acting like an honest broker, Trump said it's "just my touch, my feel... it’s what I do," suggesting that instinct, rather than preparation, is the key to getting Kim to spearhead the denuclearization of the Korean Peninsula. Trump also said "attitude" is the key to success in North Korea.

Early Monday morning, Secretary of State Mike Pompeo said Trump is heading to the summit with "confidence and a positive attitude," and that the only outcome the United States will accept is full "denuclearization" of North Korea.

The stakes surrounding Tuesday's summit are enormous. North Korea's nuclear weapons program has been the country's single domestic priority for more than half a century, and their nuclear arsenal is the only bargaining chip Kim has as a means of getting what he wants.

Experts believe Kim may be seeking relief from decades of crippling sanctions from the West, however very few take seriously the idea that Kim will give up his nuclear weapons.

One major concern is that Kim may have already gotten what he wanted when Trump agreed to the summit. North Korea has long sought to be placed on equal footing with the United States and other western powers. By agreeing to meet Kim without asking for anything in return, Trump may have already overplayed his hand.

In what may be the Freudian slip of the week, Fox News referred to Trump and Kim as "two dictators" on Sunday.

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“Chairman Kim once again clearly expressed his firm commitment to a complete denuclearization of the Korean Peninsula,” said South Korea’s president Moon Jae-In last month. “What is not so clear to him is how firmly he can trust the United States’ commitment to ending hostile relations and providing security guarantees for his government should it denuclearize.”

North Korea, despite being a hermit-like country that literally keeps its people in the dark, is expected to be extremely well-prepared for its meeting with the President of the United States.