Earlier that day, the British author had attended the launch of his controversial book, in which he accused Singapore's judiciary of bowing to outside pressure and applying double standards in its application of the death penalty.
He knew that the authorities did not like what he had to say.
While wealthy – often well-connected foreigners – can expect leniency, he argued in Once the Jolly Hangman: Singapore's Justice in the Dock, the poor and disenfranchised are summarily executed.
But at dawn he was woken by the arrival of three police officers who ransacked his room before taking him away for questioning.
Two days of interrogations later, Shadrake was released on bail, minus his confiscated passport, fearing he, too, was about to feel the full force of the same unforgiving criminal justice system he had lambasted in print. "They used shock and awe tactics in an attempt to terrify me into submission."
Last week the 76-year-old was convicted of contempt of court, for which he could spend up to six months in Singapore's Changi prison, when the high court sentences him this week. He also faces separate charges of criminal defamation, which carries a maximum penalty of two years in prison and a hefty fine. Shadrake's crime was to challenge the enthusiastic use of the death penalty in a country notoriously intolerant of dissent. Drawing on interviews with a retired chief executioner, lawyers, former police officers and human rights activists, his central claim is that justice in one of the world's most advanced economies is anything but blind.He highlights several inconsistent applications of the law which, he says, prove Singapore's judiciary "picks and chooses how they respond depending on the state's diplomatic and economic interests".
In handing down the guilty verdict, the judge, Quentin Loh, said Shadrake had "scandalised" the judiciary through "a dissembling and selective background of truths and half-truths, and sometimes outright falsehoods".
He offered the prolific British author the chance to "make amends", but Shadrake was unrepentant. "They are effectively asking me to apologise, but I have done nothing wrong and I have no amends to make," he said. "It's utter nonsense - I haven't scandalised anyone. "I'm not going to run away or back down. If they want to jail me, then so be it." Past experience suggests that Shadrake should have taken the advice of the British high commission in Singapore and excused himself from the book launch.
The country's elder statesman, Lee Kuan Yew, whose son is now prime minister, has frequently used strict anti-defamation laws to crush dissent and punish foreign journalists.
A Wall Street Journal editor was fined $10,000 last year for publishing articles deemed to have shown contempt for Singapore's judiciary, while three local activists were sentenced to short prison terms for wearing T-shirts illustrated with a kangaroo dressed as a judge.Shadrake's conviction has thrown into sharp relief the contradiction at the heart of Singapore's rise from colonial backwater to economic powerhouse: that the gains that have given its people the highest living standards in Asia since it declared independence from Britain in 1963, co-exist with an unapologetic contempt for freedoms taken for granted in other developed Asian economies.
The government is also highly sensitive to attacks on its draconian attitude towards serious crime. According to Amnesty International, Singapore, a country of nearly 5 million, has the highest per capita rate of executions in the world, having put more than 420 people to death since 1991.
In a 2004 report, Amnesty said the death penalty was disproportionately used against migrant workers, drug addicts and poorer people.
"Singapore's drug laws flout global fair-trial standards by shifting the burden of proof to suspects," says Lance Lattig, a researcher on Singapore for Amnesty in London. "A drug trafficking suspect faces hanging unless he can manage to prove his innocence. If the Singapore government has issues with Shadrake's book, it should address his arguments directly, not threaten him with prison."
Shadrake has admitted one minor inaccuracy in his book, but insists the rest of the material is "devastatingly accurate"."They know the book is accurate, which is why they're going to all this trouble," he said.
As he waits to learn his fate, the former Fleet Street journalist, who arrived in Singapore in 2002 to write travel articles for the local tourist board, admits to fantasising about swimming along the causeway and over the border to Malaysia, visible from his hotel room.
But he has no intention of fleeing: "I am prepared to go to jail: if I apologise, or try to abscond, it means I lied, that I got my facts wrong."
With his client's biggest day in court only days away, Ravi is concerned about the toll the trial is taking on Shadrake's health. He suffers from high blood pressure and an irregular heartbeat, and in August he spent two days in hospital after a longstanding colonic complaint caused internal bleeding.
Shadrake, meanwhile, insists he is in good spirits, even managing to belt out a defiant karaoke version of "My Way" on the night of his conviction.
And while the British high commission in Singapore has offered only "words of comfort" since his arrest, he says he has received countless messages of support from ordinary Singaporeans. "The authorities overreacted without thinking through the consequences and the anti-Singapore hysteria that followed," he said. "And that is growing all the time."
Shadrake refuses to reveal how he will respond if he is sent to prison this week, saying only that he has several back-up plans in place: "This story is never going away. I'll keep it on the boil for as long as I live. They're going to regret they ever started this."