The United States is in the middle of a divisive election in which both candidates have campaigned on a platform that spells a shrinking global footprint for the superpower.
It is not the only major country in the process of losing its appetite for free trade and flirting with the idea of turning insular.
This rising tide of isolationism fuelled by domestic pressures manifested itself dramatically in June with Brexit - Britons voting to leave the European Union.
Closer to home, a rising China appears to be increasingly flexing its muscles. Most recently, it has taken to pressuring smaller countries behind the scenes to adopt its stance on its territorial claims in the South China Sea.
Worse, this may completely cripple Asean if China is able to sway one or more member countries to take its side, causing the grouping to fail to come to a consensus on issues.
None of these trends is favourable for Singapore which, as a small country, benefits from globalisation and banding together with neighbours and therefore champions both of those things.
Yet it is not inconceivable that Asean could splinter, or that the US withdraws from the region, or that China grows so strong that it becomes the dominant player in the region. In such a world order, how would Singapore respond, and what are some alternative paths open to a small island nation?
OLD PRINCIPLES, NEW STRATEGIES
Diplomats and observers The Sunday Times spoke to say that Singapore has anticipated some of these global developments.
Ambassador Ong Keng Yong, executive deputy chairman of the S. Rajaratnam School of International Studies, says: "We take the world as it is and have no illusion about international politics."
But some constants remain.
As Ambassador Chan Heng Chee, chairman of the Lee Kuan Yew Centre for Innovative Cities, notes: "We believe in the rule of law and abiding by international law and the peaceful settlement of disputes. Small countries need international law, otherwise might becomes right."
While Singapore might not change its principles, it is likely to adapt them to the changing world.
Amid the rebalance, for instance, it is all the more going to stick to its principles of championing international order and the rule of law.
And although the 12-nation Trans-Pacific Partnership (TPP) trade pact may be stalled, Singapore will continue to seek strong trading partners elsewhere - for instance, India - or sign bilateral trade treaties of its own.
In India earlier this month, when Prime Minister Lee Hsien Loong was asked if he was hedging his bets against false dawns, he replied: "I am trying to bet on all the good horses."
India, he added, has had fits and starts, but has made a lot of progress since 1990.
Singapore and India upgraded their bilateral relationship to that of a strategic partnership last November, and Singapore is also in a Comprehensive Strategic Partnership with Australia.
Such ties would be useful should Asean experience a slowdown in growth. Singapore is also reaching out to establish and strengthen partnerships elsewhere, in continents where it has not had a strong presence till recently.
In fact, it is already making inroads in parts of the world previously less explored and seeking new opportunities for growth there.
As senior fellow William Choong of the International Institute for Strategic Studies puts it: "In finance, you don't only invest in stocks, you invest in bonds and mutual funds and other structured instruments. Likewise, Asean is not the only basket we've invested in.
"Singapore has very cleverly over the years - although you wouldn't hear it from a diplomat - cultivated not only its linkages to Asean but also to other parts of the world."
For instance, President Tony Tan Keng Yam made a state visit halfway across the world to Mexico in June, the first by a Singapore head of state to a Latin American country. While there, he called Mexico a good gateway for Singapore to grow its presence in Latin America, and pitched Singapore as a springboard for Mexico to enter Asia.
Taking presidential trips as a proxy of Singapore's foreign policy agenda, it shows that Singapore is keeping an eye on the Latin America region even though it is far away.
Mexico may also be a kindred spirit in that it is one of the 12 countries that are part of the ambitious TPP Singapore has been championing.
Singapore has also been maintaining its ties to the Nordic countries, finding common ground in preventing the melting of polar ice caps and understanding the implications that new trade routes opening up would have on Singapore's status as a sea port.
All this fits Singapore's strategy of diversification, which could well be extended in the future.
"We want to be friendly to everyone who is friendly to us," says Dr Choong. "We don't lash ourselves to the mast of any one power, but to all the ones that matter."
Singapore can also beef up its ties with partners such as Russia and the Middle East, building on PM Lee's trips to Russia for the Asean-Russia summit in May, and to Jordan, Israel and the Palestinian Territories in April.
ASEAN REMAINS A CORNERSTONE OF FOREIGN POLICY
That said, Singapore - a tiny island in a tough neighbourhood - will still prioritise Asean.
Even though the regional grouping has come under pressure and criticism from outsiders for internal disagreements when it comes to issues such as the South China Sea, the grouping has much to celebrate when it turns 50 next year.
For one thing, South-east Asia has remained relatively peaceful since the end of the Cold War. Asean members have also remained largely in control when it comes to major issues in the region, and established the Asean Community last year.
Mr Ong, who was Asean secretary-general from 2003 to 2008, notes that Singapore has worked with other Asean states to position the grouping as a neutral regional body engaging all major powers interested in South-east Asia.
"Asean also avoids taking sides in any disagreement among the major powers and upholds the principle of not being a proxy of any external power," he says.
Significantly, with hundreds of meetings yearly at various levels - from youth exchanges to ministerial conferences - Asean has engendered a deep layer of cooperation that cuts across multiple fields, from agricultural and environmental partnerships to cooperation in financial services and cyber security.
Adds Mr Ong: "Of course, there will be bumps on this journey of regional camaraderie, but staying together will provide the ballast."
He reckons a strong Asean is key to maintaining the growth trajectory of South-east Asia, which will motivate American enterprises, and by extension the US, to stay in the region despite growing domestic pressures.
"The challenge is to develop good reasons and strategic gains for the US to continue in South-east Asia and grow with Asean," he says.
But some observers wondered about the relevance of the grouping, after its members were unable to reach agreement on a united or strong position at some meetings on the South China Sea.
Dr Choong suggests that instead of clinging tightly to the criterion of consensus, for instance, Asean could evolve the "Asean minus X" principle, where a decision can still be made even where one or two members opt out. He points out that some scholars are already talking about such a move.
"The general principle of this proposal is that Asean shouldn't be held hostage by one or two members. A position can be that of not all 10 members, but of the majority.
"Asean is mature enough to acknowledge its differences, rather than having debacle after debacle of not releasing a statement at all because of internal divisions," he says.
Dr Choong thinks that if anything, Singapore is the only country that can suggest historic reform when it comes to decision-making within Asean.
Some might caution against such moves, as the principle of consensus remains the foundation for equality among the 10 member states. But Dr Choong feels they may be worth considering at a time when the external environment becomes more uncertain.
For now, though, with China and India continuing to grow, there is a growing incentive for member states to stay in Asean, which straddles both Asian powers, says Mr Ong.
Hopefully, Singapore's diplomats will be able to strengthen the grouping further in the face of a more challenging future when it takes over the rotating chairmanship in little over a year, in 2018.
As PM Lee put it in Japan last month: "We hope for the best but we prepare for all eventualities."