They have been hailed as a success story in tackling the virus - two places where there have been almost zero or only single digit Covid cases since the start of the year.
But this month, Singapore and Taiwan both saw a sudden and aggressive increase in cases - Singapore recorded 248 new cases last week, and Taiwan 1,200 local cases of infection.
The two have each implemented increasingly stringent restrictive policies, limiting the number of meetings and closing schools.
By world standards these numbers may seem small - but for these two regions they were unthinkable just a few months ago.
'There is clearly a sense of complacency in Taiwan'
Taiwan was one of the first countries to ban foreign visits not long after China reported the emergence of the virus - and strict border restrictions still apply in the country.
But at the local level, people are starting to become complacent - as has been done by the Taiwanese government.
Hospitals have stopped aggressive testing of citizens for Covid, even those with fever - a common symptom of the virus, according to National Taiwan University Associate Professor Lin Hsien-ho.
According to the online publication Our World in Data, Taiwan carried out only 0.57 tests for the virus per 1,000 people in mid-February - compared to Singapore which carried out 6.21 tests and Britain 8.68 during around the same period.
"There is a general assumption, even for people showing symptoms, that it is unlikely that they will be exposed to Covid-19," Dr Lin told the BBC, adding that it stems from the belief that the virus will not be able to cross Taiwan's strong borders.
"Doctors don't take it seriously, hospitals aren't vigilant, they don't do a lot of contact tracing. There's definitely a sense of complacency."
The highlight was when Taiwan relaxed quarantine requirements for unvaccinated airline pilots from 14 days to five days - and then only three days.
Shortly thereafter, there was a new cluster explosion related to the presence of China Airlines pilots who had stayed at Novotel near Taoyuan Airport.
Many of those associated with this cluster were later found to be exposed to the British variant, known as B117.
The virus then spread throughout the community, and eventually spread to Taiwan's "tea houses" - adult entertainment venues.
"People are singing, drinking, often making indoor contact without ventilation arrangements. It's not just in one teahouse, but many other shops on the same street - it's a super big spread event," said Dr Lin.
Professor Chen Chien-jen, epidemiologist and former Vice President of Taiwan, said the fact that many people who tested positive refused to claim they had visited such adult entertainment establishments made contact tracing more difficult.
"It just reminds us that even when a small part of the population breaks the rules, it will lead to leakage," said Dr Chen.
He also added that Taiwan failed to learn from the case of the entertainment industry for adults in Japan - which at one point was also a hotbed of infection - before being ordered to shut down.
"We did not learn from Japan and reflect that Taiwan may have the same problem," he said.
According to Associate Professor Alex Cook of the National University of Singapore (NUS), the Taiwan situation is "a reflection of the constant risk of a strategy that places too much emphasis on border controls and does not take enough action to prevent spread within the country".
What happened in Singapore?
In Singapore, however, the story is different.
Actions here have always been strictly restricted even if the case is low - public gatherings are limited to eight people, clubs are not allowed to open, and there are still restrictions on mass gatherings, such as weddings.
But there are still gaps in vaccine guidelines, and by the end of May, Singapore's Changi Airport - which also boasts a popular shopping mall - had turned into the country's largest Covid cluster this year.
Authorities later found that a number of infected airport staff worked in a zone that accepts travelers from high-risk countries, including South Asia.
Some of these workers then continued their activities by eating at the airport food court - which is open to the public - and spread the virus further.
Singapore currently closes its passenger terminal to the general public.
Many of those infected were later found to be exposed to the highly contagious variant that first appeared in India - known as B1617.
- 43-year prison sentence given to a woman by a Thai court for insulting the monarchy could be seen as a "warning shot" to protesters demanding reform in kingdom