Returning to the US from a G20 summit in Russia this weekend, he was faced with doing some special pleading to war-weary Americans while simultaneously pulling out all the stops to win over political allies and rivals alike for military action on Syria.
The US cannot "turn a blind eye" and Syria "would not be another Iraq or Afghanistan," Obama insisted yesterday in his weekly radio and internet address, previewing arguments he will make in a nationally televised address on Tuesday.
"Any action we take would be limited, both in time and scope - designed to deter the Syrian government from gassing its own people again and degrade its ability to do so," Obama said.
A week ago, in the wake of the August 21 poison gas attack allegedly carried out by forces loyal to Syria's President Bashar al-Assad that killed 1429 people, Obama said he felt limited strikes in Syria were needed, but added he wanted to ask Congress to authorise the use of military force.
Neither Democratic nor Republican lawmakers have been enthused about the prospect, partly because Americans strongly oppose getting involved in another Middle Eastern conflict.
Last week a Reuters/Ipsos poll said 56% of Americans believed the United States should not intervene, while only 19% supported action.
In many respects Obama is damned if he does and damned if he doesn't act. As one commentator pointed out in the influential US current affairs magazine Foreign Policy: "To some, he is acting too rashly, not allowing enough time for international inspectors to make their case, for international partners to align behind the United States, or for diplomacy to work. And still to others, Obama is the Ditherer-in-Chief, having fecklessly wrung his hands while Syria burned, while 100,000 died, while chemical weapons were used repeatedly, and while extremists congregated on the burning battlefields turning that country into the training ground for a new generation of bad guys."
All of this must be giving the president sleepless nights ahead of a Congress vote on the administration's request to use military force in Syria that could well put the future of Obama's presidency on the line. Should the President lose that vote - a distinct possibility - it would hobble him in affairs both foreign and domestic, particularly if fellow Democrats collaborate in his defeat.
At home, Obama's "political capital" will be severely tested. With every victory or defeat, US presidents gain or lose that capital, especially if they have been personally engaged in the issue at stake. For the moment at least, the question of how Obama's domestic ratings might fare should he lose the vote is still the subject of some speculation. On the international stage, however, the significance of defeat is much more clear-cut and goes way beyond Syria.
For Obama's national security team, a congressional "no" vote this time around would weigh heavily against seeking future congressional approval should the president feel the need to use force again if, say, the Iranian nuclear standoff comes to a head or North Korea escalates its provocations to new levels. Politically hamstrung in this way, some analysts also highlight how it would make it more likely that a terrorist group might use illicit weapons.
According to David Rothkopf, CEO and editor at large of Foreign Policy magazine, it comes as no surprise that Syria's supporters, like Russian President Vladimir Putin or China, would oppose Obama's proposed strikes. Both nations regularly seek to check the application of American power.
As Rothkopf adds, however: "It must also be chastening for the president that some of America's strongest allies, like the United Kingdom, are saying, "You're on your own on this one, old boy."
Yesterday there were at least a few encouraging signs for Obama on the European front, when the European Union's foreign policy chief Catherine Ashton said the EU's 28 nations agreed that available information seemed to show strong evidence that the Syrian government carried out a chemical attack on civilians in August.
"[The government] is the only one that possesses chemical weapons agents and the means of their delivery in a sufficient quantity," Ashton told reporters after meeting EU foreign ministers in the Lithuanian capital of Vilnius.
The ministers agreed, she said, that the world "cannot remain idle" and said a clear and strong response was needed to prevent any future use of chemical weapons in Syria.
But they stopped short of lending support to the military action proposed by the United States and France. Germany too said it would sign a Group of 20 statement that calls for a strong international response, agreeing a day after other European powers because it wanted to ensure unity within the European Union.
The absence of Germany's signature on Friday's statement, which also falls short of supporting a military strike, sparked criticism at home that Chancellor Angela Merkel was abandoning Germany's allies to avoid alienating voters. Germany holds a federal election in two weeks, and the electorate overwhelmingly opposes military action in Syria, while international allies insist on German support.
Meanwhile, as the debate around whether the US Congress and international community should authorise military action against the Syrian regime has focused on a potential strike, others are pushing to dramatically increase the supply of weapons to Syrian rebels as well.
Washington already has such a programme in place through the CIA, but the Obama administration has proposed shifting responsibility for arming and training the rebels to the Pentagon, which has units specifically designed for this type of operation and the logistical capability to pull it off.
While such a programme would likely put the rebels on more equal footing with forces loyal to the Syrian regime, it could have long-term repercussions.
According to the independent US intelligence think-tank Stratfor, a rapid, massive increase in the flow of weapons into Syria would inevitably result in guns falling into the hands of fighters who Washington fears would use them against US interests in the future. Because of this risk, the imperative to keep the Syrian civil war and its long-term consequences manageable will be a major factor in framing US decisions about whether and how to more forcefully intervene.
It was following an alleged chemical weapons attack in Syria in June that the United States agreed in principle to arm the rebels.
Since 2012, the CIA has overseen the vetting and supplying of rebel groups with assistance from other countries such as Qatar and Saudi Arabia. However, as a clandestine organisation the CIA has found it necessary to outsource much of this operation to third parties.
Weapons have indeed made it to Syria and been used to some effect, but the arming process has been slow and the volume delivered so small that their impact has been minimal.
Shifting this operation to the Pentagon and making it overt would rapidly accelerate the flow of weapons to the rebels. It is simply better placed to move large volumes of weapons, along with specialist trainers who can teach rebels how to use them.
Dangers in such a strategy remain, however: not least that it would be impossible to fully vet and control the movements of weapons once they are inside Syria.
Such weapons could be modified by enterprising fighters or arms dealers and subsequently used against Western interests. This happened in Afghanistan during the guerrilla war against the Soviets and more recently in the wake of the Libya conflict in 2011, with sophisticated arms making their way to into the hands of Islamist insurgents in West Africa.
Other factors will also be contributing to Washington's assessment of the extent and nature on any proposed intervention. On Friday the State Department, apparently concerned about possible strikes on American targets by Syrian government allies in the region, ordered nonessential diplomats at the United States Embassy in Beirut and their families to leave Lebanon.
The moves appear to reflect concern that supporters of the Syrian government, like Hezbollah or Iran, might carry out or encourage terrorist attacks on United States diplomats in retaliation for an American-led military strike
According to the Beirut-based Daily Star newspaper, pro-Hezbollah Sheikh Afif Nabulsi was recently quoted as saying that "any [US] strike against Syria would be met by harsh responses against US interests in the region."
This, of course, could all be bluff on Hezbollah's behalf. Should the threat be for real, however - and most likely it is - those responses would probably involve a wave of assassinations and hostage takings in Lebanon along with the targeting of other US assets and citizens in the region.
To that end there have already been reports of talks between Iranian diplomats and Hezbollah leaders, in much the same vein as coordination between Hezbollah and the Damascus regime has operated over battlefield operations inside Syria itself.
Hezbollah has long had operatives capable of undertaking missions aimed at US interests in Lebanon and beyond, including in the United States. Some within the US intelligence community have even warned that Hezbollah's operatives are better trained and more numerous than any group al Qaeda has ever controlled or deployed.
Faced with all of these factors, President Obama finds himself in a diplomatic no man's land caught between a rock and a hard place both politically and militarily.
"His current track doesn't offer a Goldilocks solution that can be seen as just right because it is neither too much nor too little, too fast or too slow. It doesn't win the centrist seal of approval just because it is discomfiting to those on the far right and the far left," points out David Rothkopf.
Recognising Obama's dilemma and criticising his performance so far on Syria is one thing, but coming up with alternative strategies is something else entirely. That much even his most vociferous detractors would admit. If military intervention and force is not the answer, diplomacy is the only other option.
Both the UN Secretary General Ban Ki-moon and independent conflict monitoring organisations like the International Crisis Group have stressed the need to avoid further militarisation of the conflict and revitalise the search for a political settlement.
They, however, are not the President of the United States. A president who has already made clear that Syria has crossed a "red line" through its use of chemical weapons.