Scott Morrison has been confronted by the serious trade and security risks of moving Australia's embassy in Israel to Jerusalem during his first foray onto the world stage.
The prime minister has also been forced to tread a delicate tightrope between jostling global superpowers China and the United States.
Mr Morrison was intent on developing international ties during a series of meetings at the East Asia Summit in Singapore this week.
He delivered a strong statement on regional security during high-level talks with regional leaders, expressing concerns about militarisation of the South China Sea.
He urged restraint and encouraged the nations caught up in territorial disputes to conclude negotiations on a code of conduct while raising the risks posed by North Korea and humanitarian crisis in Myanmar.
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There was some progress on trade with negotiations on an ambitious 16-nation pact "80 per cent complete" and likely to be done with by the end of next year, Mr Morrison said.
But it was his idea to shift the Israeli embassy that caused him diplomatic pain.
Malaysian Prime Minister Mahathir Mohamad delivered a stark warning about the security risks.
"I pointed out that in dealing with terrorism, one has to know the causes. Adding to the cause for terrorism is not going to be helpful," Dr Mahathir said.
Indonesia - the world's most populous Muslim nation - is also furious and has put a major Indonesia-Australia trade deal on hold until the issue is resolved.
After meeting President Joko Widodo on Wednesday, Mr Morrison committed to finalising a review of the embassy site before Christmas.
Labor Leader Bill Shorten said he'd made Australia "look stupid" by contemplating the move but the prime minister shrugged it off.
"Australia will determine our foreign policy issues and we'll consider those in our time frame on our terms," he said.
Competition between the US and China for dominance in the Indo-Pacific loomed large over the Singapore summit.
Mr Morrison insisted "Australia doesn't have to choose and we won't choose".
He met with Li Keqiang while in Singapore, with the Chinese premier noting the occasion marked a "turning point" after a year of frosty relations.
Mr Morrison has offered to help Beijing bankroll infrastructure projects in the Pacific and is expected to meet President Xi Jinping at the APEC Summit in Papua New Guinea this weekend.
While in Singapore, New Zealand Prime Minister Jacinda Ardern renewed a long-standing offer to resettle at least 150 refugees from Nauru.
Mr Morrison recently indicated he may be open to the deal but has since gone cold.
He also confronted Indian Prime Minister Narendra Modi over an ongoing sugar dispute crippling Australian farmers.
Mr Morrison departs for Darwin on Thursday night for a historic meeting with Japanese leader Shinzo Abe.
