He had gone in and out of jail for around 30 years, mainly for drug-related offences.
But support from The Helping Hand has helped Mr Kumarakuru, 47, stay out of jail for four years - the longest that he has kept out of trouble since he was 17.
Mr Kumarakuru, who goes by one name, took part in a cycling event yesterday to tell more people about the good work done by the halfway house in supporting former inmates and their families.
Around 200 cyclists took part in Ride To Restore, a not-for-profit collaboration between The Helping Hand and interest group My Bike Group, to raise awareness of the Christian halfway house and promote cycling as a healthy hobby among its residents.
Participants could choose to complete a 94km round-island route or 40km "fun ride", with their registration fees paying for a jersey, logistics and a post-race lunch in the halfway house.
Assistant manager Fong Wai Chuan, 42, a co-organiser of My Bike Group, said he hopes this is the first of more activities with the halfway house. The group organises activities for people interested in helping society through cycling events.
"I think most people don't know what The Helping Hand does, and may be nervous that we are former inmates," said Mr Kumarakuru, who now helps with operations at the halfway house. He used to interact with customers of the halfway house's furniture store, one of its social enterprises.
This is part of the halfway house's work therapy to prepare residents for gainful employment after their release from prison. It can take in up to around 95 residents, mostly former drug offenders, with around 30 of them serving the last six months of their terms.
"Maybe this event will help people to see what we are doing and how we are working hard to change our lives," said Mr Kumarakuru.
While he was the only ex-offender among cyclists at the event, his fellow residents served as road marshals and hosted the post-event lunch in the halfway house.
Many participants, including nurse Christine Chung, said they did not know much about the halfway house's work and social enterprises before signing up for the event, which started at Upper Serangoon Road, where the halfway house is located.
"When I passed by The Helping Hand in the past, I always thought it just sold teak furniture. It never crossed my mind that they were helping people in other ways," said the 37-year-old, who took on the 94km route.
Ms Chung, who cycles with friends at least thrice a week, said: "Ex-offenders live with labels and, hopefully, even if it's just a small group of us, we can help to build public awareness."
Seow Bei Yi