An accused stalker breached bail conditions by contacting his alleged victim through bank transfer messages in a "clever and concerning manipulation of the process".
"This outlines the irrationality of conduct which is alleged," Chief Magistrate Lorraine Walker said on Friday.
Sean Martin Russell was released into the community despite ignoring another judicial officer's "stern warning" about breaching his conditional liberty.
The 20-year-old man hugged his mother in the ACT Magistrates Court public gallery and sobbed after being granted bail on the condition he leaves the territory.
Shortly after, he greeted a media camera by displaying his middle finger.
Russell denies charges of stalking, damage property, dangerous driving and two counts of common assault.
The man is accused of stalking a woman for more than a year before police arrested him in May, when he was released on several conditions, which included not contacting her.
However, he did so by sending her multiple bank transfers of $1 or $5 with descriptions that included allegedly threatening and harassing messages.
Russell also breached conditions that he not harass the woman, be within 100 metres of her or enter her suburb of residence.
The day before police arrested him again last month for the breaches, the man drove past the woman's home and called her multiple times.
"You know what's coming," Russell was recorded saying during one call.
"You're lucky I'm not allowed in that f---ing suburb or I would have been pulling up and you f---ing know what would have, c---, coz you know what's going to be in my car this time and he's f---ing dead, c---!"
The Chief Magistrate said the allegations against Russell were "very concerning" and detailed "violent and controlling behaviour in both private and public places".
The alleged victim previously told police she was so scared of Russell "she could no longer leave her house alone" and that he had, on numerous occasions, been violent and threatening.
Among many examples of alleged stalking behaviour, the woman told police she had received 117 phone calls in one day from a "no caller ID number" she suspected to be Russell's.
That day, he allegedly followed her in his car, "driving very dangerously", and attempted to get into her vehicle, yelling and hitting the windows, once at a stop sign and again after swerving in front of her car.
He also allegedly smashed the car window of a man who witnessed the "road rage incident".
Prosecutor Michael Gemmell said conditions would not ameliorate risks, like endangering the safety of the alleged victim, involved in granting Russell bail, and opposed the application.
Defence barrister James Maher said his client proposed to move to Queensland, "far away from the complainant", and that the man understood he was on a "short leash".
Under his bail conditions, Russell can only enter the ACT for court or pre-arranged legal appointments and must check into his local police station daily.
"If he's checking in there every day, we know he's at a safe distance," Ms Walker said.
The court heard Russell had already spent close to five weeks in custody for the alleged offences.
"You know what's at stake if you mess up. I can't stress enough to you that it will likely see you put back in custody at great speed," Ms Walker said.
"Don't throw your life away for some stupid reason."
Russell is set to return to court for a multi-day hearing in November.
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Support is available for those who may be distressed. Phone Lifeline 13 11 14; MensLine 1300 789 978; 1800-RESPECT 1800 737 732.
