When new prisons chief Desmond Chin takes office on Oct 1, it will buck the trend of senior police officers being parachuted into the job, which has lasted nearly 30 years.
Mr Chin is a career prisons officer with almost 26 years' experience.
The Ministry of Home Affairs (MHA) announced last Friday that the 50-year-old will succeed current boss Soh Wai Wah, 52, who is set to take up the post of principal and CEO of the Singapore Polytechnic.
The practice of seconding top police officers to head the Prisons Department began with Mr Tee Tua Ba. Mr Tee, now 74, served as director of prisons from January 1988 to 1992. But unlike the four others who succeeded him directly in subsequent years as prisons chief, Mr Tee spent time as director of prisons (special duties ) understudying the role before taking over.
He served with distinction and went on to become police chief. After that, he was made Singapore's ambassador to Brunei. He is currently non-resident Ambassador to Switzerland and also serves as chairman of the Singapore Red Cross Society.
The prisons chief job was then known as "director of prisons" until it was changed in recent times to "commissioner of prisons".
Unlike Mr Chin, who hails from the National University of Singapore, his two immediate predecessors and current incumbent all started off in their careers as Ivy League scholarship holders.
Mr Chin has held various posts in prisons, rising through the officer ranks. He has been Superintendent of Changi Prison and worked in the MHA and as chief executive officer of the Singapore Corporation of Rehabilitative Enterprises.
In a 2013 Home Team Journal article, he said: " We also believe that society's goals are better achieved through humane treatment and rehabilitation of prisoners, giving them hope and a second chance at life upon release, so they do not go back to crime.
"But make no mistake, prison life remains highly regimented and conditions are spartan to deter inmates from ever wanting to come back."
Retired prison officers contacted lauded Mr Chin's appointment, noting that it affirmed prospects for a career officer with suitable ability to reach the top.
Retired senior officer S. Raveendran has seen five prison chiefs come and go in his time. "Mr Chin has worked his way up from the ground, and his appointment shows this is an important factor that has been recognised," he said. "This is the first such move in nearly 30 years for a directly recruited prisons officer to reach the top through sheer capability and personal effort."
Mr Chin will take over from Mr Soh, who has overseen the significant enhancement of the Singapore Prison Service's capabilities and effectiveness, according to the MHA.
He was responsible for launching the Yellow Ribbon Community Project, which mobilises grassroots volunteers to help families of those incarcerated, and also set up the Community Rehabilitation Centre for young first-time drug abusers.
There were some 9,602 convicted prison inmates and 1,255 remand inmates as of last December, according to the Prisons website.