Singaporean law allows caning to be ordered for over 30 offences, including hostage-taking, robbery, gang robbery with murder, drug use, vandalism, and rioting. Caning is also a mandatory punishment for certain offences such as rape, drug trafficking, illegal money-lending, and for visiting foreigners who overstay their visa by more than 90 days, a measure designed to deter illegal immigrant workers.

Caning is in practice always ordered in addition to a jail sentence and never as a punishment by itself. It is administered in an enclosed area in the prison, out of view of the public and other inmates. Those present are limited to the inmate, prison wardens, medical officers, the caning officer and sometimes high-ranking prison officials to witness the punishment.

An inmate sentenced to caning receives no advance warning as to when he will be caned, and is notified only on the day his sentence is to be carried out. In the caning room, the inmate is ordered to strip naked and receives a medical examination by the prison doctor to check whether he is medically fit for caning, by measuring his blood pressure and other physical conditions. If the doctor gives the green light, the inmate then receives his caning, but if he is certified unfit for punishment, he is sent back to the court for his prison term to be increased instead. A prison official confirms with him the number of strokes he is to receive.

The inmate is then led to the A-shaped frame (called a "caning trestle") and his wrists and ankles secured tightly to the frame by strong leather straps in such a way that he assumes a bent-over position on the frame at an angle of close to 90° at the hip, with his posterior protruding. Protective padding is placed on his lower back to protect the vulnerable kidney and lower spine area from any mis-strokes so that only his buttocks are exposed to the cane. The officer administering the caning takes up position beside the frame and delivers the number of strokes specified in the sentence, at intervals of 10 to 15 seconds. He is required to put his full force into each stroke. The strokes are administered all in one caning session, unless the medical officer certifies that the inmate cannot receive any more strokes because of his condition, in which case the rest of the strokes are converted to additional prison time.