Today, the judge amended one of his supervision conditions to "test the waters" by giving him "some level of independence".
Judge O'Driscoll told the teenager that he would "trust you to do the things you are asked to do".
The teen was praised for showing "a degree of maturity" by telling the court that he did not want to return home for Christmas because he saw it as a "high-risk situation".
A report from Community Corrections last month raised "a couple of negative things", which resulted in the judge telling him he had to keep his emotions in check.
The teen had invited the judge, police, and Crown for a festive season BBQ at his supervised accommodation but the judge said he'd have to see a good positive report before anyone would come.
The teen is due back in court for a further judicial monitoring update on January 16.