Orlando was not expected to survive seven years ago, when he was born at 23 weeks.
Now thriving, the Tharawal Public School Illawong pupil has not only caught up to his peers, he is on track to helping other bubs who followed in his first tiny footsteps.
On October 27, he will again join his family in Walk For Prems - an annual event where Australians walk together in support of the 48,000 premature or sick babies born in Australia every year.
Celebrating its 10th walk this year, the event is the largest annual fundraiser for the Life's Little Treasures Foundation, a charity dedicated to supporting the families of babies born sick or before 37 weeks gestation.
Orlando's mother, Menai's Stephanie Stojanovski, 32, went into labour at 23 weeks. Orlando spent four months in special care.
"I started bleeding and by the time I got to hospital, my cervix was open," she said.
"There was no way of stopping the labour. I had no warning signs. The survival rate was low, we were given all the talks.
"He only weighed 696 grams and was almost doll-like. He had to be on ventilation because his lungs were extremely underdeveloped. He was also born with his eyes fused shut because they hadn't opened yet.
"Orlando went through 13 blood transfusion and two infections but we were very lucky with feeding - he didn't have any gut problems and met all his milestones within his corrected age when we came home.
"In winter he gets a croupy cought as his lungs are still healing. Doctors say it will take at least until he's eight for the lungs to repair. But he runs around like normal kids - rides his bike, his scooter."
"We have done this event pretty much every year since he was born. Orlando wants to raise money himself. He's already raised nearly $600."
Mrs Stojanovski's younger daughter, Ava, was also pre-term, but not as early.
"Ava got to 36 weeks," she said. "I was well monitored. My cervix started to shorten at 30 weeks, so I was on bed rest. When she was born, she just had jaundice."
The federal government announced this week that it would invest in a world-class clinical trial focusing on conditions affecting preterm baby lungs.
It will put forward funding from the Medical Research Future Fund International Clinical Trial Collaborations program.
The Murdoch Children's Research Institute will receive $1.4 million to investigate the best ways to support fragile lungs in preterm babies, which are prone to collapse and cause injury from the first time they breathe.
While positive end-expiratory pressure (PEEP) at birth is essential to support the preterm lung, this project will conduct the first large clinical trial of PEEP strategies in preterm infants.
This clinical trial will provide important guidance to clinicians across all health care settings worldwide.
Premature birth is on the rise. It occurs in about eight per cent of births compared with six per cent in the past.
Causes can include increasing maternal age, multiple pregnancies with assisted reproduction, higher rates of maternal diabetes and obesity.
Walk for Prems has raised more than 1.8 million and this year Life's Little Treasures Foundation hopes to raise $350,000.
Participants will also pause to show their respect for the families whose babies have sadly died.
There will be children's activities including music, a jumping castle and face-painting at the Sydney event, being held at Jubilee Park, Glebe.