Hong Kong (CNN)Joshua Wong is getting used to being in court.
A month ago, Hong Kong's most high-profile pro-democracy activist was joking with his co-defendants and waving at family as the Court of Final Appeal granted him leave to challenge a six month jail sentence he received in August. On Thursday he was one of 16 in the dock, facing another, separate jail term.
That case was adjourned to a later date several hours into proceedings as judges needed more time to review a mountain of evidence provided in support of light sentences for the young defendants.
Wong's cases are among the dozens brought by prosecutors against pro-democracy protest leaders and lawmakers in the wake of 2014 demonstrations which shut down parts of the city for months on end.
These prosecutions, brought by the Hong Kong government and supported by its Beijing masters, are having a chilling effect on dissent and scaring the young protesters who had previously been the backbone of the pro-democracy movement away from politics, observers say.
"People who would otherwise be happy to join in and take part are now thinking twice," says Jason Ng, a member of the Progressive Lawyers Group, a pressure group.
"(They're thinking) it's really not worth putting my career at risk when the potential benefit is close to nothing."
Kong Tsung-gan, author of "Umbrella: A Political Tale from Hong Kong," Kong has tracked almost 40 civil and criminal cases against pro-democracy figures, some of which have already resulted in imprisonment, fines, and disqualification from the city's parliament.
He told CNN the scale and scope of the prosecutions, particularly the tough sentences for those convicted, are "unprecedented."
In the past, he said, "it has been the case that one activist here and another there would be prosecuted, and perhaps convicted of unlawful assembly and the like, but the person would normally receive a fine or a prison sentence not greater than three weeks."
Antony Dapiran, a Hong Kong lawyer and author of "City of Protest," said the "incessant slow drip of legal action over the course of this year has been... effective in keeping pressure on activists who do not know what and when the next government action will be, and (that is) therefore having a stifling effect on their activities."
A spokesman for Hong Kong's Department of Justice said "allegations of political prosecution or persecution are entirely unfounded," adding the DOJ is "committed to safeguarding the rule of law and judicial independence in Hong Kong, as well as keeping criminal prosecutions free from any interference."
The sheer number of cases has seen the city's pro-democracy movement enter a repetitive and energy-sapping cycle of court hearings, protests against the prosecutions, and vigils outside prison or judicial buildings.
While tens of thousands took to the streets to protest the initial jailing of Wong and other protest leaders -- including Nathan Law, who was the city's youngest lawmaker until he was disqualified from office in July -- demonstrations since have been somewhat lackluster.
Around 1,800 people joined a march led by Wong Sunday, which he had billed as perhaps his last part to protest with his supporters before he returned to jail.
Wong told the South China Morning Post he was "tired" and wanted to enjoy his "last weekend" before returning to jail.
"I'm satisfied that a group of Hong Kongers walked with me in my last rally today although not a lot of people came out," he said.
"It doesn't really matter to us how many people came out as long as we did our best and provided an opportunity for our supporters to show solidarity," pro-democracy icon "Long hair" Leung Kwok-hung -- who was also disqualified from office earlier this year -- told the paper.
Dapiran said the prosecutions were designed "to make the cost of dissent intolerably high, and to make in particular Hong Kong's politically active youth think twice about whether they are willing to pay an increasingly steep price -- jail, bankruptcy, the effect all of that might have on future careers -- to express their political views."
The 2014 protests were largely driven by high school and university students, who took to the city's streets in huge numbers and camped out for weeks on end. A small number of them went on to become lawmakers in 2016 elections. Of the cases Kong tracks, more than 60% of those facing prosecution are under 30.
"They want to say, If you confront us, we will destroy your life," Kong said.
Hong Kong's DOJ rejected the suggestion that it was prosecuting an unprecedented number of cases.
"The Occupy Movement is an unprecedented situation which involves a large number of participants," a spokesman said, referring to the 2014 protests. "The DOJ does not intentionally prosecute more people than it should do so."
While prosecutors have found themselves well equipped to bring cases against protesters, thanks to draconian laws inherited from the British colonial administration, Beijing has recently put pressure on the city to pass new regulations further tightening restrictions on speech.
In particular, China's government has taken a harsh line on advocacy of Hong Kong independence, with President Xi Jinping warning in a visit to the city earlier this year such talk was a "red line" for Beijing.
In October, China introduced a new National Anthem Law, which punishes those who "disrespect" the song with up to 15 years in jail. That move comes after Hong Kong football fans repeatedly booed and jeered the "March of the Volunteers" as it played before their international matches.
More booing took place at a World Cup qualifier against Lebanon last month, and fans displayed banners with slogans like "Hong Kong is not China."
While the Chinese law currently does not apply to Hong Kong, it is being adopted into the city's statutes, and an amendment to the original law which would extend the punishment to a maximum of three years is being considered by Beijing.
Hong Kong must accept it is part of "red China" and led by the Communist Party, a top Beijing official said during a visit to the city this week, following comments by another central government representative that Hong Kongers who challenge the party "have brains made of granite."
As Beijing takes a far tougher line against dissent within Hong Kong, many are fearful of the return of a proposed anti-sedition law which was defeated by mass street protests in 2003.
Article 23 of Hong Kong's constitution, Basic Law, calls on the city's government to "enact laws on its own to prohibit any act of treason, secession, sedition, subversion against the Central People's Government," but so far, repeated administrations have dragged their feet on doing so.
Hong Kong already has laws against treason and sedition, but critics of Article 23 believe the criminalization of subversion and secession could enable the prosecution of a wide range of dissenting voices, particularly those who advocate or endorse Hong Kong independence.
"Trust in the Hong Kong government, not even to mention the (Communist) Party, is so low that any introduction of Article 23 legislation will be viewed as an attack on civil liberties," Kong said.
"In theory, Article 23 legislation could be used to effectively outlaw a broad spectrum of the pro-democracy movement."