On Monday, Mayor London Breed announcing the city is stepping up efforts to clear encampments.
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The move coming after local leaders said they received clarity from a federal court about an injunction which limited their clearing response.
It's just the latest development in a months-long legal battle between the city and homeless advocates.
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"This lawsuit and this injunction has put the city in an impossible situation," said David Chiu.
Chiu is the San Francisco City Attorney.
He says the court gave the city the okay to clear encampments as long as they first offer shelter to those living on the streets.
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Chiu believes it's a step in allowing the city to enforce its own laws.
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"San Francisco has really tried to balance providing compassionate services and shelter to unhoused individuals with maintaining healthy and safe streets. But that balance was really upset particularly as over half of the folks who have received offers of shelter would turn it down," he said.
Others, though, have concerns.
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That includes Jennifer Friedenbach, the director of the Coalition on Homelessness - the group suing the city.
"Our whole intent of the lawsuit is really to get more folks off the streets," she said.
Friedenbach claims even before the court's clarification, the city was never prohibited from cleaning up encampments.
However, she worries the increased sweeps could lead to the city violating its own rules on clearing encampments.
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Friedenbach specifically pointed to policies prohibiting the destruction of homeless people's property- which she says can be counterproductive.
"Criminalization in general does not lead to an exit out of homelessness, and it in fact usually lengthens homelessness," Friedenbach said.
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The legal battle is far from over though, with more trial dates on the issue set for the months ahead.
Until that time comes, Friedenbach says, she wants real solutions.
"We're looking for a much more thoughtful response that has increased number of people getting off the streets."