The territory is grappling with this crisis since its handover to Beijing, many residents fret over what they see as China's closing grip.
Hong Kong: Exasperated with the government's unflinching attitude to escalating civil unrest, Jason Tse quit his job in Australia and jumped on a plane to join what he believes is a do-or-die fight for Hong Kong's future.
The Chinese territory is grappling with its biggest crisis since its handover to Beijing 22 years ago as many residents fret over what they see as China's tightening grip over the city and a relentless march toward mainland control.
The battle for Hong Kong's soul has pitted protesters against the former British colony's political masters in Beijing, with broad swathes of the Asian financial centre determined to defend the territory's freedoms at any cost.
Faced with a stick and no carrot - chief executive Carrie Lam reiterated on Tuesday protesters' demands were unacceptable - the pro-democracy movement has intensified despite Beijing deploying paramilitary troops near the border in recent weeks.
"This is a now or never moment and it is the reason why I came back," Tse, 32, said, adding that since joining the protests last month he had been a peaceful participant in rallies and an activist on the Telegram social media app.
"If we don't succeed now, our freedom of speech, our human rights, all will be gone. We need to persist."
Since the city returned to Chinese rule in 1997, critics say Beijing has reneged on a commitment to maintain Hong Kong's autonomy and freedoms under a "one country, two systems" formula.
Opposition to Beijing that had dwindled after 2014, when authorities faced down a pro-democracy movement that occupied streets for 79 days, has come back to haunt authorities who are now grappling with an escalating cycle of violence.
"We have to keep fighting. Our worst fear is the Chinese government," said a 40-year-old teacher who declined to be identified for fear of repercussions.
"For us, it's a life or death situation."
What started as protests against a now-suspended extradition bill that would have allowed people to be sent to mainland China for trial in courts controlled by the Communist Party, has evolved into demands for greater democracy.
"We lost the revolution in 2014 very badly. This time, if not for the protesters who insist on using violence, the bill would have been passed already," said another protester, who asked to be identified as just Mike, 30, who works in media and lives with his parents.
He was referring to the 79 days of largely peaceful protests in 2014 that led to the jailing of activist leaders.
"It's proven that violence, to some degree, will be useful."
Nearly 900 people have been arrested in the latest protests. The prospect of lengthy jail terms seems to be deterring few activists, many of whom live in tiny apartments with their families.
"7K for a house like a cell and you really think we out here scared of jail," reads graffiti scrawled near one protest site. HK$7,000 ($893) is what the monthly rent for a tiny room in a shared apartment could cost.
The protests pose a direct challenge to Chinese leader Xi Jinping, whose government has sent a clear warning that forceful intervention to quell violent demonstrations is possible.
Some critics question the protesters' "now or never" rallying cry, saying a crackdown by Beijing could bring an end to the freedoms in Hong Kong that people on the mainland can only dream of.
The campaign reflects concerns over Hong Kong's future at a time when protesters, many of whom were toddlers when Britain handed Hong Kong back to Beijing, feel they have been denied any political outlet and have no choice but to push for universal suffrage.
"You either stand up and pull this government down or you stay at the mercy of their hands. You have no choice," said Cheng, 28, who works in the hospitality industry.
"Imagine if this fails. You can only imagine the dictatorship of the Communists will become even greater ... If we burn, you burn with us," he said, referring to authorities in Beijing.
"The clock is ticking," Cheng added, referring to 2047 when a 50-year agreement enshrining Hong Kong's separate governing system will lapse.
As Beijing seeks to integrate Hong Kong closer to the mainland China, many residents are recoiling.
A poll in June by the University of Hong Kong found that 53% of 1,015 respondents identified as Hong Kongers, while 11% identified as Chinese, a record low since 1997.
With the prospect of owning a home in one of the world's most expensive cities a dream, many disaffected youth say they have little to look forward to as Beijing's grip tightens.
"We really have got nothing to lose," said Scarlett, 23, a translator.
As the crisis simmers, China's People's Liberation Army has released footage of troops conducting anti-riot exercises.
But graffiti scrawled across the city signals the protesters' defiance.
"Hong Kong is not China" and "If you want peace, prepare for war" are some of the messages.
Tse said he believes violence is necessary because the government rarely listens to peaceful protests.
"Tactically I think we should have a higher level of violence," he said. "I actually told my wife that if we'll ever need to form an army on the protester side I will join."