On one front, the strategy appears to be working: The number of new cases in the community has inched downwards since April 7, with 22 cases reported yesterday.
But this progress has been hard-won and the battle is far from over. As Prime Minister Lee Hsien Loong noted in a Facebook post yesterday, the next few days will be critical for Singapore.
One lapse in the community could spark a new cluster, which could spiral and be hard to control, as has happened, both here and elsewhere.
It has also taken Singaporeans some time to adapt to the incremental tightening of rules on the ground.
Day One of the circuit breaker saw more than 7,000 people issued written advisories for breaching stricter safe distancing measures.
Nearly 3,000 people were issued such advisories on Day Four, with more than 40 people fined $300 each for their second offence.
That day, sports stadiums were also closed after people ignored warnings to stop exercising there in groups.
And by Day Six, the Government decided that even first-time offenders would be fined. Around 200 people were fined that day - the same number as were fined yesterday on Day Twelve.
The ball is now in Singaporeans' court, said infectious diseases expert Leong Hoe Nam.
"We see a drop in the numbers, and it shows that most people are obeying the circuit breaker rules," he said. "But this isn't good enough. We need it lower."
The next few days will be critical because they determine the direction that Singapore will take next, say experts.
In the best-case scenario, the existing circuit breaker measures work and they are lifted when the situation improves.
In the worst-case scenario, the circuit breaker measures are further tightened and extended beyond May 4 - a possibility the Government has already hinted at.
The most likely scenario is that circuit breaker curbs will be selectively reduced, if the evidence shows which measures have worked to minimise community spread, said Adjunct Associate Professor Phua Kai Hong from the National University of Singapore's Lee Kuan Yew School of Public Policy.
In particular, the evidence must show that the outbreak is under control among foreign workers, he added.
Both he and Dr Jeremy Lim, who is co-director of global health at the National University of Singapore's Saw Swee Hock School of Public Health and chief executive of a gut microbiome startup, highlighted the issue of transmission at dormitories housing foreign workers.
"Vigilance is crucial now as the outbreaks in the dormitories can spill out into the rest of the population," Dr Lim said.
"What's vital now is that people not just adhere to the circuit breaker measures but also support the workers in the dormitories."
This could be in the form of encouragement or financial support for workers, Dr Lim added.
Dr Leong said for the everyday Singaporean, their responsibility is to do what they can to prevent the virus from spreading further. He added that a person who protects himself against the virus is also protecting Singapore.
"You wear a mask and you wash your hands and you don't touch your face. With that, you have done your part and blocked the infection," he said.