In a city looking less like a hub of commerce, and more and more like a conflict zone, Hong Kong's chaos has reached a new level.
And it now has the casualties to match.
As protestors surrounded a police officer, his colleague responded with a single shot.
An 18-year-old student was struck in the chest with a bullet fired from close range.
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A demonstrator who went to his aid was tackled, while a petrol bomb was hurled at police.
The student was taken to hospital in a critical condition after the bullet penetrated his lung.
Fears of such violence have been growing since Hong Kong's pro-democracy protests began.
But this is the first time anyone's been shot, and it came on China's national day.
"Today I am sad, our national day is supposed to be a day to celebrate and be happy," said Stephen Lo Wai-chung, Hong Kong's Police Commissioner.
At the same time, China's troops and tanks paraded through Beijing to Tiananmen Square.
Thirty years after the Tiananmen crackdown Hong Kong is the source of rebellion now.
"I hope the CCP, the Chinese Communist Party will fall," said one protester.
"This is only the Communist Party's happy day, it's not us," said another.
The protest began peacefully, with hundreds of thousands marching in black through Hong Kong's streets.
But it soon devolved into ugly clashes, with 180 people arrested as protestors set fire to train stations and vehicles.
They hurled both petrol bombs and bricks and in reply were met with tear gas and water cannons.
And now the response includes bullets too.
It's a dangerous step for a city in crisis, where fear is building for what comes next.