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It is an intuitive observation that rehabilitative sentencing options such as probation and reformative training (“RT”), designed as they are for young people, ought to be made available in the justice system in sentencing young offenders. Where the challenging task of the court lies is in determining which young offenders ought to be able to avail of such sentencing options and which offenders should not. To this end, our courts have continually refined the analytical approach to be adopted for this task. From as early as 1965, Ambrose J in Tan Kah Eng v Public Prosecutor [1965] 2 MLJ 272 observed that as far as possible, first offenders under the age of 21 years should not be subject to a sentence of imprisonment “unless the offence is so serious that a sentence of imprisonment has to be imposed”. This consideration of the seriousness of the offence was supplanted by Yong Pung How CJ in Siauw Yin Hee v Public Prosecutor [1994] 3 SLR(R) 1036 to include scrutiny of an offender’s response to rehabilitation: when considering the appropriateness of a rehabilitative sentence, the court should take into account not just an accused’s expression of remorse but also evidence of the accused’s previous response to attempts at rehabilitating him, such as past flouting of probation conditions (at [7]).