Australia's most decorated living soldier spent the night in Sydney's Silverwater prison after he was dramatically arrested and charged with two counts of the war crime of murder and three counts of aiding or abetting the same charge.
He did not appear at a brief, online NSW Bail Division Court hearing on Wednesday, when his case was first heard and his lawyers did not make an immediate application for his release.
They tried instead to have the matter listed for an in-person hearing at the city-centre Downing Centre Local Court for later in the day but conceded that might not be possible.
"We understand that's a bit of a pipe dream," his lawyer Jordan Portokalli told the bail court.
The judge agreed and re-listed the matter for June 4, meaning the Victoria Cross recipient will remain in custody for at least two months.
The 47-year-old is accused of the murder of unarmed civilians while deployed in Afghanistan between 2009 and 2012.
It's alleged three victims were shot by subordinate members of the ADF, in the presence of, and acting on the orders of Roberts-Smith.
While Roberts-Smith's courtroom travails began in 2017 when he unsuccessfully sued Nine newspapers for defamation, legal experts say his case moving to the criminal realm could be a watershed for war crimes prosecutions in Australia.
The prospect of a criminal trial for alleged offences committed overseas in the theatre of war was almost unprecedented in modern times, former president of the Australian Human Rights Commission Gillian Triggs said.
"It's a very technical area of law and we have had very few examples in Australian national practice that would provide some precedents," Professor Triggs told AAP.
She said Australia's failed prosecutions of multiple alleged Nazi war criminals in the 1990s prompted authorities to be extremely cautious before launching criminal action.
But with two men now charged for alleged war crimes committed in Afghanistan, the floodgates of prosecutions might now be ready to open.
Another former SAS soldier, Oliver Schulz, was charged in 2023 with the war crime of the murder of a young man in Afghanistan in 2012.
He has maintained his innocence.
"These (trials) would ... strengthen the willingness of justice department prosecutors to say 'we've got the evidence here and we'll go forward with it'," Prof Triggs said.
Roberts-Smith's case will be monitored internationally, Prof Triggs said, with the decision to charge at home taking the matter out of the hands of war crimes prosecutors at the International Criminal Court.
However, before the case proceeded to any potential trial, Australian prosecutors would need to solve some complex legal problems, an international law expert said.
"A long time has passed, so that delay itself can create challenges in terms of collecting reliable evidence," University of Queensland international law professor Rain Liivoja told AAP.
"The fact that the alleged crimes were committed overseas, and indeed in a location to which there is no easy access, makes the collection of evidence even more difficult."
A Federal Court judge previously found Roberts-Smith was responsible for a number of killings but those findings were made on the balance of probabilities, rather than the criminal standard of beyond reasonable doubt.
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