How will America bring Russia to heel over Syria?
Not so long ago, Rex Tillerson was the head of Exxon Mobil.
Years were spent dealing with Russia, so much so he was honoured with an award of friendship from President Putin.
Fast forward to his appointment as US Secretary of State and deciding where on the mantle to put that commendation must have been quite a quandary - especially in an administration publicly accused of cosying up to the old enemy.
Aware of the toxic nature of the allegations, the former oil man has sought to separate himself from old friends.
However, he could be forgiven for packing his gift from Putin as he heads back to Russia - via the G7 in Italy - to seek potentially the trickiest deal of his career.
The exact detail of the message he will be delivering will be thrashed out over the next 24 hours after discussions with his fellow foreign ministers.
That at least is the European spin, though the Americans may feel they are already clear in what they wish to say.
Either way, up for discussion at the G7 is how to bring Russia to heel.
By that, representatives of the UK, Germany, Italy, France, Japan, Canada, the US and EU, mean they want Russia to lessen support for President Assad while stopping further attacks and moving towards a negotiated peace.
Long term the aim is a transition to elections and a representative government but no one doubts just how long term achieving that aim is.
Quite what leverage could be used to gain Russian support is what will be discussed amid the ancient walls of Lucca.
The wish is for soft power - sanctions or perhaps a promise of return to the G8 from which Russia was ejected following the annexation of Crimea.
Soft power hasn't delivered hard results so far - but as last week's air strikes proved, hard power can no longer be assumed to be a hollow threat.