Three months into his presidency, Trump's sternly nationalistic and isolationist rhetoric has Australia questioning whether it can continue to count on the US, testing one of the world's closest alliances.
"There's a great sense of loss about the America that we thought underpinned the security order (and) that the America we relied on might not be there," Mathew Davies, head of the international Relations Department at the Australian National University, told CNN.
Trump is due to meet Australia's Prime Minister Malcolm Turnbull in New York City Thursday, their first meeting since their heated phone conversation in February, which shook the two countries' relationship.
Since then high-profile US officials have worked hard to smooth tensions, including a visit by Vice President Mike Pence in April, but many questions remain ahead of Trump and Turnbull's meeting.
"All of those values we thought were settled and agreed, are they actually agreed?" Davies said.
"What is Australia's role in the Asia Pacific? Should we continue to see ourselves as a close ally of the US or should we look at what Australia wants?"
Australians 'concerned' by Trump presidency
Australia's leaders were not ready for a Trump presidency, former Liberal Party leader John Hewson told CNN.
"I was amazed, they didn't even have a number to call him to congratulate him. They had to get (former golfer) Greg Norman to give them a phone number to call Trump," he said.
Australians as a whole appeared apprehensive about a Trump presidency. According to a 2016 poll by the Lowy Institute, almost half of the respondents said Australia should distance itself from the US if Trump won, while only 42% said the US alliance was "very important," the lowest in eight years.
A poll taken less than two weeks before November's election by Essential polling found 79% of Australians would be "concerned" by a Trump presidency.
"I think there's kind of a perverse fascination with this rogue in the White House, but I think there's a lot of distrust about what that means," Sydney University Department of History professor James Curran told CNN.
He said that though the US-Australia alliance was still "healthy," there were difficulties that needed to be resolved.
"While meeting on board an old aircraft carrier in the United States will show a very close defense relationship, it shows a sentimental view of the past rather than a close look at the troubles in the relationship going forward," Curran said of the scheduled Trump-Turnbull meeting.
Australia is torn between the US and China, the former as its close ideological ally and the latter as its primary trading partner.
A third of Australia's exports in 2015 were sent to China, worth approximately $62.3 billion.
Many experts have said Australia would be forced to choose between the two superpowers, but Curran said Australia should maintain relations with both.
"The more difficult question for Australia is how does it help the US accept that China has its own strategic sphere in Asia and that shouldn't be seen as a threat," he said.
While Trump and Chinese President Xi Jinping have struck increasingly warm rapport over North Korea and Taiwan, the new US style of diplomacy could cause long-term issues for Australia, Davies said.
"There's an accommodation between China and the US on the basis of their immediate interest, or at least Trump's immediate interest ... the US isn't defending the world order that we thought the US was there to defend," he said.
"If the US is only ever going to be involved because it gets something out of it, that's very different to being involved (over shared values)."
What would Australia do in war?
As the possibility of conflict on the Korean Peninsula looms and Trump contemplates greater action against ISIS, Hewson said Australia needed to ask itself if it would go back into war with a Trump-era America.
Both countries have fought together in every major conflict of the 20th century, including both World Wars, the Vietnam War and Iraq War.
"The alliance always needs to be tested. I'm all for having a very clear idea about our own national interest and not having to take sides if we don't want to," Hewson said.
It is getting "harder and harder" for Australia to refuse US requests for military aid, as US expectations of its ally grow, Curran said.
"We've now got US marines rotating through Darwin, so I think we need to have that conversation about what extent America's expectations are going to be realized," he said.
Hewson says it is time for Australia to pursue a new diplomacy, building relations with its Asian neighbors, such as Indonesia and Japan, and moving away from the US.
"It's a different world and the volatility is hard to take ... we have to be very conscious of what's in our national interest and what is not and act accordingly," he said.