Iran's supreme leader has threatened to pull his country out of the nuclear deal and resume enriching uranium if European countries do not promise to buy Iranian oil and to oppose all new US sanctions against Tehran.
Three days after US secretary of state Mike Pompeo delivered America's extensive list of demands of Iran for a new nuclear agreement, Ayatollah Khamenei laid out his own demands of European countries for Iran to stay in the 2015 deal.
"If the Europeans hesitate in responding to our demands, Iran is entitled to resuming its nuclear activities," he said.
The sweeping demands are likely to be rejected by Britain, France and Germany - diminishing the already narrow hopes of saving of the 2015 nuclear agreement.
The ayatollah made five demands, calling on them to "guarantee the total sales of Iran's oil", meaning Europe must promise to make up for any oil sales from third countries which are cancelled because of US sanctions. Such a guarantee would potentially cost Europe billions of dollars.
The ayatollah said European banks "must guarantee business transactions with the Islamic Republic", even in the face of US sanctions. European banks that continue to deal with Iran could be blacklisted and frozen out of the American financial system.
He called on the Europeans to issue a UN security council resolution condemning US president Donald Trump's decision to leave the deal and Europe "must confront imposition of any sanctions on the Islamic Republic and stand firmly against US sanctions".
Finally, he said Europe "must guarantee it will not raise the issue of the Islamic Republic's missiles and regional affairs".
The ayatollah may have staked out a deliberately demanding position to give more room for the Iranian foreign minister, Javad Zarif, to appear conciliatory in his own meetings with the Europeans to try to save the nuclear agreement.
Mr Zarif and other reformist figures are eager to preserve the deal, while more hardline politicians and elements with the Revolutionary Guard want to see it scrapped. The supreme leader has the final decision.
But if Iran's real red lines are even close to the sweeping demands made by the ayatollah it is unlikely the Europeans will be able to satisfy Tehran.
A UK Foreign Office spokeswoman did not directly address the ayatollah's demands but said the UK, along with the EU, "continues to view the nuclear deal as a vital factor in our shared security".
The two positions staked out this week - one by Mr Pompeo and the other by Ayatollah Khamenei - leave a narrow and treacherous path for European diplomats as they try to salvage the 2015 agreement.
Mr Pompeo said the US would inflict the "strongest sanctions in history" on Iran unless it agreed to 12 American demands, including withdrawing from Syria and halting its funding of militant groups like Hizbollah and Hamas.