Arguably most important among those questions: How long can it practically sustain such draining financial support for Ukraine?
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That thought is not new, but is increasingly echoed privately in some corners of officialdom. It also reflects several current grim truths.
The war has been deadlocked for some time, while last week, Ukraine was forced to withdraw from the key town of Avdiivka after months of fierce fighting, marking its worst defeat since the fall of Bakhmut in May.
Money desperately needed from the United States is stuck, having passed the Senate but awaiting House approval. Unity between the European Union (EU) and NATO is starting to fray, with nearly every big decision held up and threatened with veto.
No serious Western voices want to abandon Kyiv, but it's undeniable that fatigue is setting in as the bills grow.
Since the start of the crisis, the EU and its regional allies have spent more than $100 billion funding Ukraine's defense effort, according to the Kiel Institute's Ukraine Support Tracker.
Earlier this month, EU leaders agreed to a $54 billion package for Ukraine between now and 2027. The United Kingdom, arguably the major security player in the region, has also pledged more than $15 billion to Ukraine since 2022. For context, according to the Kiel Institute the US has spent $66 billion, with another $60 billion in the pipeline.
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While the West's resounding support for Ukraine since 2022 has surprised many in the diplomatic world, the longer the war drags on, the more the fatigue grows.
Between there being no end to the conflict in sight, and competition for political attention in the Middle East - as well as domestic concerns from inflation-led cost-of-living crises around the world - spending huge sums on Ukraine could become politically harder to stomach for governments.
The political pressure on spending will become more visible as European Parliamentary elections take place in June, as well as national polls in multiple countries including the UK, a key Ukrainian ally.
European officials need only look at the difficulty US President Joe Biden is having with his own Ukraine package to see the real-world impact of funding a costly overseas war when it comes into direct contact with domestic politics.
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Adding to these inauspicious distractions is the prospect of Donald Trump returning to the White House next year.
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Trump has not clearly stated what his Ukraine policy would be, save his claim that he could end the war within 24 hours. The former president's anti-NATO rhetoric, general disdain for European institutions and odd admiration for Putin are well-known.
While no one knows what another Trump presidency might materially mean, it is plausible to envisage a worst-case scenario for Ukraine, where it loses momentum on the ground while the new occupant of the White House decides that America has spent enough already.
This is an alarming prospect for European officials who already believe Putin is digging in and trying to wait out the West.
This is where the next 12 months become crucial for Ukraine's European allies. It is manifestly in continental Europe's interest that Putin does not win this war - there are very few who would disagree with that sentiment.
It is therefore crucial, officials say, that whatever happens in America, Europeans hold their noses and keep spending, however hard it seems.
In the run-up to the US presidential election, the question of what happens to European security without America will inevitably be asked. And while it is true that Ukrainian security is directly tied to wider European security, the immediate question of how to support Kyiv is subtly different to Europe's long-term goal of greater security independence from DC.
Can Europe continue funding Ukraine if the US pulls financial support?
Most officials argue that it can. It would be difficult, sure, but possible. "The EU is very good at raising funds and there are tools it hasn't yet used," one NATO official told CNN.
The official said that in the next 12 months, Brussels should start to look at using money tied up in frozen Russian assets to help fund Ukraine. "While that money cannot legally be used to buy weapons, it can be used to cover compensation costs, freeing up money for weapons from EU and national budgets," they said.
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Diplomatic voices who have eyes on the world beyond Europe raise eyebrows at this. Some fear that setting a precedent for using frozen assets to raise money for foreign wars could give countries like China a green light to do the same in its internal regional battles. Beijing introduced a new law last year that makes it easier to do similar to foreign assets within China.
The thornier issue is whether or not Europe could provide Kyiv with the weapons it needs to win the war without American support.
The answer to that would be no. Europe simply doesn't have the manufacturing heft right now to independently serve Ukraine over the next 12 months.
However, Western diplomats are optimistic that arming Ukraine fits perfectly with a much-needed European drive to reduce its reliance on America.
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Officials point to a recent deal, brokered by NATO, where European countries have pledged to purchase 1,000 missiles from American firms that will be built in a new German factory.
Almost everyone agrees that Europe needs to buy more weapons and have a security policy that is not so reliant on the US. Achieving that needn't come at the expense of America, and dangling the carrot of lucrative contracts for US companies is one way of ensuring everyone wins.
Putin's unprovoked invasion of Ukraine is a travesty that has cost unnecessary lives. If any positives are to come from it, they should include Europe finally becoming fit to defend itself, and cooperating with its old ally.
And for what it's worth, the vast majority of Western officials believe that if Europe can spend the next year making itself fighting fit, it will be far easier to keep a future President Trump onside.
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