Giving evidence at a sentence hearing on Thursday, Muslim chaplain Ahmed Kilani said Hamdi Alqudsi had never said anything radicalised to him despite the pair chatting about 20 times since 2017 while the now convicted terror boss was behind bars.
"From my engagement with him, I have never seen anything to indicate any support for any violent extremism," Mr Kilani told the NSW Supreme Court.
Other inmates had actually turned on him, making his life difficult in prison because they did not see him as extreme, he said.
An affidavit by Mr Kilani filed with the court described Alqudsi's view of Islam as "moderate", saying the inmate had condemned those who were violent.
Crown prosecutor Trish McDonald SC argued that Alqudsi, who is incarcerated in Goulburn's supermax prison, had expressed an extremist ideology in the past and had never formally abandoned those views.
Representing the terror boss, barrister Kellie Stares SC said her client did not have to expressly disavow anything and had instead showed signs of reform by progressing from Goulburn's High Risk Management Correctional Centre to a more "mainstream" South Coast jail in 2018.
Alqudsi was only transferred back to Goulburn to make it easier for him to attend his trial last year, the court heard.
"This is not an offender who's at HRMCC and is unable to progress ... because he has religiously extreme views," Ms Stares said.
In September last year, a jury found Alqudsi guilty of directing the activities of the Shura from August to December 2014.
His plans, which were never carried out, included attacks on the Sydney Gay and Lesbian Mardi Gras, the Israeli embassy, the Garden Island Naval Base in the Sydney suburb of Woolloomooloo, and a targeted strike on the Australian Federal Police at a courthouse.
The idea of murdering a tourist and draping their body in an Islamic State flag was also mentioned.
The Shura, which means consultative or consultation council in Arabic, was formed in 2013 initially to send fighters from Australia to Syria. The group pledged allegiance to ISIS in August 2014.
On Thursday, Ms McDonald told Justice Stephen Rothman that Alqudsi's offending was serious as he was the head of an extremist organisation which targeted young men, some as young as 16.
"The role of the offender in respect of the Shura has been that he has either been described as the leader and as reflected in the verdict of the jury the one directing the activities of the organisation," the barrister said.
He had given the green light for certain planned attacks, had been persistent in the group pledging allegiance to Islamic State, and took active, clandestine steps to avoid monitoring and detection by police, she said.
Ms Stares disagreed, saying any plans the group had were in an "embryonic stage" and they were a relatively unsophisticated group of like-minded individuals, a far cry from more large-scale terrorist organisations.
"Your Honour would have seen far more sophisticated drug deals than this," the barrister said.
Targets had yet to be confirmed amidst the "brainstorming", and no real planning had been done beyond a single scouting out of the Wooloomooloo naval base, she said.
Charged in November 2019 while he was already behind bars, the court will have to determine how any jail time and non-parole period imposed fits with his current time in custody.
Directing a terrorist organisation carries a maximum sentence of 20 years.
Justice Rothman will deliver his sentence on February 20.
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