Malcolm Kysor, a no less unsavoury character, watched his guards better than they did him and fled from a Pennsylvania prison when the most complacent guard was on duty.

The breakouts of these two Americans in the past few years share several striking similarities with the recent escape of Jemaah Islamiah leader Mas Selamat Kastari. He literally seized his window of opportunity to escape from the Whitley Road Detention Centre (WRDC).

The common threads linking these escapes are: Complacency among guards, failure to observe prison protocol and inmates being able to gain the trust of those guarding them.

Mas Selamat lulled his guards into believing he was a broken man. Though uncooperative during interrogations, he was not violent.

From the day he entered the centre in February 2006, he was flagged as a dangerous man. For nearly nine months, he was handcuffed whenever he was out of his cell. But his case officer later recommended the cuffs come off.

Mas Selamat, 47, set about gaining the trust of his guards by closing the urinal door just a bit each time he was in the toilet. As they became more comfortable with that, he began to close it fully. Each time, he came out within a minute or two. And on Feb 27, he slipped out of a window while a guard waited outside the urinal door.

Vail, 40, won his guards over because he was a gifted artist and a glib talker. Over time, he charmed the prison officials, including the instructor at the jail's carpentry workshop to which he was assigned. Vail used his friendship with the male instructor to sneak tools such as screws, blades and even the head of a sledgehammer back to his cell.

Over months, he used these tools to slowly chip away at the ceiling of his cell, eventually fashioning a hole wide enough for a man. The hole led to a ventilation shaft and, together with his cellmate, Vail crawled to freedom.

Despite having raped and murdered an eight-months-pregnant woman, Vail ingratiated himself with the authorities by painting artworks for them. They trusted him so much he was allowed to move around freely, unescorted, as he painted decorations and murals at the facility. The guards even let him bring a chair into his cell. At one point, he even had his instructor breaking the rules by smuggling in cigarettes for him.

The guards escorting Mas Selamat should not have let him out of their sight, even when he was using the toilet.

It is a 'very basic rule' which every law enforcement officer is told to follow. But somehow, the Gurkhas guarding Mas Selamat did not stick to procedure.

In Vail's case, the guards at the carpentry workshop should have checked all the inmates before they returned to their cells. But they did not, and Vail knew that.

Kysor, 53, a burglar and murderer, hid in a rubbish bin and had an accomplice wheel it on to a garbage truck and out of the State Correctional Institute at Albion, Pennsylvania.

The guard responsible for inspecting the garbage truck merely checked its exterior and undercarriage. He did not prod the garbage to check if anyone was hiding in it, and he did not turn on a heart-beat monitor, which would have detected Kysor.

What was worse was that the guards who were supposed to be monitoring the surveillance cameras missed the escape even though it was captured on CCTV. It took two hours before they suspected something was amiss, and another two hours before they alerted police.

Back in Singapore, the superintendent at the WRDC had warned his guards that Mas Selamat was not someone they should take lightly. After all, he had almost escaped from a jail in Bintan where he was serving an 18-month sentence.

His ruse then: He asked to be left alone to say his prayers, and then jumped out of a first- floor window. But the police reacted in time and caught him. That jump left him with a limp - an injury which may have made the guards at the WRDC complacent.

But unlike Vail and Kysor in their respective prisons, Mas Selamat hardly enjoyed much freedom at the Whitley Road centre.

When he moved between buildings, he was blindfolded so he could not familiarise himself with his surroundings. He was always escorted by two armed guards. In addition, all walkways at the centre were enclosed, so Mas Selamat could not have learnt of his exact location.

The degree of freedom he had depended on his case officer, who was tasked to extract information from him and to assess his mental state. It was this officer who recommended that he be relieved of his handcuffs in September 2006.

The guards were told not to talk to Mas Selamat or any other inmates so that there would be no familiarity. Detainees were also not allowed to talk or even see each other.

In Vail's case, he grew so close to his guards and fellow inmates that one prison official later admitted he saw him more as a co-worker than a prisoner. Complacency also 'directly contributed' to Kysor's escape, an investigation later found. It also showed that Kysor had familiarised himself with the movements of the guards in the alley where the garbage truck was usually parked because he was assigned to work there.

This was in spite of the rule that dangerous convicts like Kysor serving lengthy sentences were not to be allowed to work there.

Further checks revealed that the practice of allowing prisoners serving life sentences into the dietary department, where Kysor worked, persisted even though there were repeated reminders of the rule. The situation was so bad that other prisoners had also stashed caches of crudely made weapons and contraband like cigarettes in the department.

Mas Selamat's escape was a salutary lesson for Singapore's guardians, who are no less infallible than guardians elsewhere.

If anything, the escape points to the need for alertness, adherence to procedures, however cumbersome, and a mind much sharper than those held captive.

cheekin@sph.com.sg