North Dakota Judge James Gion said he plans to order Greenpeace to pay expected total damages of $345m to Energy Transfer in a case connected to protests over the Dakota Access oil pipeline.

Court filings indicate he would sign an order requiring various Greenpeace organisations to pay the judgment to the midstream company.

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The judge fixed damages at $345m last year, cutting the jury’s award by roughly 50%, although the most recent filing did not state a final figure.

The order is expected to trigger appeals to the North Dakota Supreme Court by both sides.

The Dakota Access Pipeline is an underground crude oil pipeline stretching around 1,168 miles (1,880km), with a 30in diameter. The pipeline carries light, sweet crude oil from the Bakken/Three Forks Play in North Dakota, South Dakota and Iowa to Illinois.

The case arises from protests in 2016–17, when thousands gathered and set up camps near the pipeline’s Missouri River crossing upstream of the Sioux Tribe’s Standing Rock reservation. The tribe has for years objected to the pipeline, saying it endangers its water supply.

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A nine-person jury last year found Greenpeace International, Greenpeace US and Greenpeace Fund liable for defamation and other claims brought by Energy Transfer and its subsidiary Dakota Access.

The jury found Greenpeace US liable on all counts including conspiracy, trespass, nuisance and tortious interference, while it found the other two entities liable on some claims.

The jury awarded total damages of $667m, split among the three organisations, before the judge reduced the amount. Greenpeace US’ share of the jury award stood at $404m.

Energy Transfer had previously said it intended to appeal the reduced damages, arguing that the jury’s original findings and award were lawful and just.

Greenpeace declined to comment on the latest court filing, but Greenpeace US interim general counsel Marco Simons repeated that the organisation could not afford to pay the damages, reported the Guardian.

It also added that the lawsuit aims to use the courts to silence activists and critics and chill first amendment rights.

Energy Transfer has said the case concerns Greenpeace complying with the law rather than free speech. During the trial, an Energy Transfer lawyer said Greenpeace directed efforts to stop construction of the pipeline, including organising protesters, sending supplies for blockades and making untrue statements about the project.