Shelley Lee Williams (42) was jailed for five years for a spree of offending in June 2017.
She robbed a South Dunedin jeweller of $550, during which she threatened to shoot a man in the leg.
A couple of weeks later, Williams targeted Sue Todd Antiques, then followed it an hour later with the robbery of the Elgin Food Market, in Mornington.
The police breakthrough came when they raided Williams' Oamaru home.
They found clothing she had worn to commit the robberies neatly laid out in the bathroom.
The coat was turned inside out to dry, gloves and balaclava carefully draped over the bathtub and an overnight bag beneath them at the ready.
On the floor of another room lay a plastic pistol next to Williams' nail polish.
And dotted around the property were notes that revealed her criminal intentions.
"Rob = shops and jewel store. Heavy gold chains & bangles, diamonds etc," she wrote.
"Go in & don't speak. Just hand a note & point gun."
"Run to Dunedin & or Chch," another said.
"Hit fish n chip shops. Small shops holding cash day & night times."
Williams' first appearance before the Parole Board noted her "inconsistent behaviour".
She had accrued six misconducts and had tested positive for drugs.
"Ms Williams spoke candidly about her behaviour in prison and her misconducts. She said that she is not abusive to staff, but she will tell prisoners off. She agrees that she can be disruptive at times," panel convener Mary More said.
A Corrections officer who reported to the board said the prisoner needed structure and routine.
Williams could be "vocal and theatrical", but had no issues with staff, they said.
Despite the offences taking place in Dunedin and its surrounds, the sentencing took place last year at the Auckland District Court.
Williams had been at the Auckland Regional Women's Correction Facility but had since been transferred to Christchurch Women's Prison to complete the Kowhiritanga programme - group-based therapy.
She told the board the course had been "amazing" and she now realised she must never drink or use drugs again.
Although many of her previous convictions stemmed from substance abuse, Williams revealed to the Parole Board she had been sober for her most recent offending, a fact that surprised her family.
Ms More said the case was "complex".
She ordered a psychological report to be completed for the next parole hearing.
"The board is conscious that, as a transgender woman, Ms Williams may struggle with group programmes, particularly in the community," Ms More said.
Williams' current release plan was described as "weak".
She will be back before the board in July.
A report about Williams' Australian conviction history was also ordered.
