North Korea has consistently demonstrated that it is unwilling to engage in direct negotiations over its rapidly developing nuclear program despite Trump's fiery rhetoric and increased sanctions -- growing more defiant in the wake of several successful ballistic missile launches and its latest nuclear test.
While top diplomats continue to insist the US prefers a diplomatic resolution to rein in the rogue nation, there is little evidence to indicate that either side is willing to concede any ground on key issues that could open the door to formal negotiations.
The absence of official diplomatic talks has only increased the likelihood of a potential miscalculation
, according to several experts, noting that Trump's sometimes unpredictable threats of "fire and fury" and a "devastating" military option have been publicly contradicted at times by several of his top advisers hoping to strike a more cautious tone.
But amid the bluster, North Korea has attempted to engage in what the US qualifies as "track two" talks to facilitate conversation beyond formal diplomatic channels and it is not unusual for intermediaries to approach American scholars or ex-officials with particular political ties when a new administration takes office.
The White House is aware when these meetings occur and provided with any information that might be gathered, according to experts who have engaged in talks.
Outreach by North Korean government officials started in January after Trump's inauguration with the goal of gaining a broad understanding as to how the new president's policies might differ from those of the previous administration, according to several experts who were approached.
"They wanted to get a beat on the new president ... but that did not happen," said Douglas Paal, a member of President Ronald Reagan and George H.W. Bush's National Security Council staffs who was contacted on several occasions by the North Koreans this year.
The Washington Post
first reported that North Korean officials were reaching out to several Republican-linked analysts to get a better understanding of Trump's messaging.
"I think they may have thought that reaching out to people who represent what is now the mainstream way of thinking and had who had more access to the Trump administration than people in past was a better way to send messages or get information," said Bruce Klingner, a former CIA analyst and the top expert on North Korea at the conservative-leaning Heritage Foundation.
"They are trying to piece together what they can about what the US policy is under the new administration," he said. "But even in Washington, we are often confused or have questions about what the parameters of the policies are, so imagine trying to assess Washington from further away, in Seoul, Tokyo, and Pyongyang."
Klingner declined an invitation from North Korea's mission to the United Nations to visit Pyongyang for meetings but he has participated in multiple conferences involving North Korean officials.
"They are trying to discern what the policy is and possible triggers for red lines," Klingner told CNN, adding that efforts to contact conservative or Republican analysts are likely the result of confusion over the Trump administration's messaging in the absence of official diplomatic talks with the US government.
While these talks can provide valuable opportunities for both sides to gather information, Klingner emphasized that the North Koreans should use official channels to communicate any messages that might signal they are serious about negotiations directly to the US government.
The US has communicated directly with North Korea at times through its mission to the UN -- known as the "New York Channel."
Communications through this channel were cut off in July 2016 but re-opened to facilitate the return of Otto Warmbier -- an American student who had been imprisoned in North Korea, according to Klingner, who added that efforts to engage in track two talks did not just begin with the Trump administration or while the channel was closed.
North Korea's mission to the UN did not respond to CNN's request for comment.
However, Trump and Kim's war of words has coincided with an uptick in outreach by North Korean intermediaries seeking to establish alternate channels of communication -- but experts said they noticed a shift in tone from the North Koreans in recent months compared to meetings earlier this year.
While Klingner declined an invitation to travel to Pyongyang, he did meet with North Korean officials in June during a conference in Sweden.
"The North Koreans were much more self-assured than they had been in previous meetings," Klingner said, adding that the message seemed to be that "denuclearization was completely off the table and there was nothing the US or Seoul could offer that would change that."
That point was only emphasized as North Korean officials became irritated when American experts began to float possible ideas for a compromise, Klingner said.
Paal also said that the North Koreans seemed unwilling cede ground when he was approached about a possible meeting in August and viewed these meetings as an opportunity to repeat their terms.
"Our conclusion was they are still not serious about talks," Paal told CNN, adding that he thinks North Korea won't stop until it is nuclear capable.
And evidence suggests Pyongyang is approaching that capability at a more rapid pace than previously thought following a string of successful ballistic missile launches and its sixth nuclear test earlier this month.
But from the outside looking in, some experts said the North Koreans are continuing to reach out to these American analysts because Trump has caught Kim off guard with his bluster and there is a real concern about what could happen next.
According to Bruce Bennett, a senior researcher at the RAND Corporation who specializes in North Korea, Kim may have alluded to this point during his televised response to Trump's speech to the UN General Assembly this month when the President warned the US would "totally destroy North Korea" if forced to defend itself or its allies.
In a rare televised address, Kim admitted that Trump's remarks defied his own expectations before noting that "a frightened dog barks louder."
"I believe that North Korea has sought to 'deter by bluster' or 'coerce by bluster' for years," Bennett said, adding that Pyongyang's rhetoric has largely been threats that they "lacked a will to execute."
"But they have to worry that President Trump may have that will ... his efforts to reach out to US conservatives also suggests a degree of desperation," he added.
The internal pressure to maintain his "god-like" image could also be a contributing factor to Kim's attempts to better understand Trump's intentions, according to Bennett.
"Yes, Kim appears really worried about what Trump might do. But I suspect he is even more worried about how what Trump says and does will undercut Kim internally, especially with the North Korean elites," he said.