VICE News is appealing an Ontario court's decision to force its reporter to hand over communications he had with an alleged Islamic State fighter.

The appeal comes as a newly unsealed police document provides insight into why Canada's federal police force is making its demands. It also serves as an intimate portrayal of how the 22-year-old Calgary man, who is wanted on terror charges, transitioned from a "normal kid" to an outspoken jihadist who championed violence.

Last month, an Ontario court upheld a production order granted to the Royal Canadian Mounted Police (RCMP) by the court in 2015 for all Kik instant messenger chats, or screen shots of the chat logs, and any other type of communication between national security reporter Ben Makuch and Farah Shirdon, a Calgary man believed to have left home in 2014 to fight alongside IS militants in Iraq and Syria. The order also demands any notes or records from all VICE employees or third parties regarding how Shirdon was contacted and any interviews that were facilitated.

A number of civil liberties and press freedom advocates around the world have slammed the order and the court's decision as an affront to journalistic integrity, arguing that reporters should not be treated as an extension of law enforcement.

The production order was sought following a number of articles Makuch wrote in 2014 based on his interviews with Shirdon, and a video interview between Shirdon and VICE CEO Shane Smith. In those interviews, Shirdon declared that terrorist attacks would be carried out by IS in Canada and New York City.

Canadian authorities then charged Shirdon in absentia with several terrorism-related offenses. His exact whereabouts are currently unknown. The RCMP argues that Makuch's communications are vital evidence needed to prove their charges as well as Shirdon's location.

'The whole family was very upset with Shirdon's actions and believes that he was brainwashed by someone to be acting in this manner.'

The court has now lifted the sealing order on the RCMP's 102-page application for the production order, also known as an Information to Obtain (ITO), which outlines its reasons for seeking records and notes from Makuch and VICE — and outlines the force's broader investigation into Shirdon. Many parts of it have been redacted.

RCMP Constable Harinder Grewal, who authored the ITO, states he prepared it using information from 11 other RCMP officers, most of whom work on the Integrated National Security Enforcement Team (INSET). The force began its investigation into Shirdon in August 2014, after a National Post article referenced a video of Shirdon burning his Canadian passport and threatening Canada and the US.

After the passport-burning video was written about, RCMP investigators spoke with Shirdon's mother, Nura, and sister, Idil, multiple times in Calgary in 2014. "The whole family was very upset with Shirdon's actions and believes that he was brainwashed by someone to be acting in this manner," the ITO states. "There were no signs of any changes in his behavior and his inclination towards religion had brought positive changes in his life and no one had or could have predicted that he would do such a thing."

According to the document, Nura told investigators her son was just a "normal kid" who "enjoyed his TV, hanging out with his friends, playing video games etc." Shirdon did not excel at school, likely because he had too many friends, she thought, but he planned to graduate from the Southern Alberta Institute of Technology that year with a minor in business.

Shirdon wasn't religious until 2012, when he took an interest in Islam and began attending a mosque downtown. Nura noticed he improved at school and became more respectful of her and "paid more attention to his life."

But things took a turn in March 2014, a few months after Nura moved to Saudi Arabia to be with her husband, Shirdon's father. She says Shirdon phoned her and said he was in Turkey and "wanted to live in a Muslim country."

When Nura asked him why, he replied, "I am sorry and don't be sad," before the call got disconnected.

In two interviews with investigators in 2014, Shirdon's sister Idil told them he is in contact with their father in Saudi Arabia, and that he has tried to persuade him to come home. She said at the time she believes her brother may be in Syria.

The ITO states that Idil said Shirdon had since called their mother to say he does not want to return home, but "will not break ties with the family, further that he loves them all and that his decision to leave had nothing to do with the family."

The ITO also goes into great detail about Makuch's articles on Shirdon, who was prolific on multiple public social media platforms and used a number of pseudonyms; the document identifies 12 of them. It also delves into Makuch's professional roles at VICE, his social media presence, and other information including the location of the car he's registered to drive.

Makuch told VICE News in an interview he was struck by the breadth of evidence on Shirdon in the ITO.

"I think one thing it really illustrates is that the RCMP has a lot of evidence against him, and that my evidence isn't the only evidence that they have," he said. "It's clear that I do not have information related to an imminent threat on national security."

The ITO shows the RCMP's investigation into Shirdon is based on open source information unrelated to VICE, Shirdon's activities on social media platforms such as Twitter and Instagram, and interviews officers conducted with members of his family.

Further, the RCMP successfully obtained information through court orders it served to Kik Interactive, Wind Mobile, and Air Canada.

But, the ITO claims that the communications from Makuch and VICE are crucial to proving the charges against Shirdon. For example, it says the notes around how the video interview was set up between Shirdon and Shane Smith is "vital context evidence to prove that [Shirdon's] implicit admissions and murder and his stated threats of further violence and murder were done sincerely as opposed to the actions of a foolish or mentally unstable individual enjoying the hubris of internet celebrity."

Regarding Shirdon's public presence on Twitter, the ITO states: "Through the social networking sites, Shirdon confirmed that he was with the ISIS and getting paid by them. He also demonstrated that he was in a combatant role and posted his pictures with weapons."

'This case is setting a very dangerous precedent.'

The RCMP foresaw the ramifications of it compelling a reporter to hand over materials.

"It is a reasonable inference that this news organization would not be able to stage this kind of interview with a purported member of a terrorist group if they had a reputation for immediately handing original evidence to the police," the ITO concludes.

For Makuch, the contents of the document reaffirms his decision to continue fighting.

"It's mind-blowing to think that there's been this large investigation and that they need my evidence in order to convict somebody who isn't even in the country," he said. "The justice system is going to have to do some soul-searching about how they want to situate journalists in society. Because this case is setting a very dangerous precedent."