Bob Kaufman considers himself an expert at living on San Francisco’s streets.
For roughly a quarter of a century, the 70-year-old has slept in an RV in the city. He has developed a routine of avoiding street sweepers and police. He has learned the ins and outs of the city’s tow yards and the quirks of the judges to whom he has to appeal in order to retrieve his two vehicles.
But in November, the rules of engagement for him and the more than 500 San Franciscans who live in camper vans will change as the city rolls out a two-hour parking ban on vehicles longer than 22 feet or taller than 7 feet.
As the deadline nears, Kaufman’s list of questions has grown longer.
“How are they going to enforce it? Are they going to put signs on every block of the city?” he asked. “They’ve already towed both of my vehicles several times. It’s always like you’re dealing with a bunch of robots.”
Soon, for Kaufman and others living in their vehicles, that metaphor may become literal.
The city is exploring the launch of an AI chatbot meant to answer the questions of vehicle dwellers affected by the impending parking ban. The technology, first reported by Mission Local (opens in new tab), is being tested, the mayor’s office confirmed, without providing details.
“It’s degrading,” Kaufman said. “It’s like saying we’re not worth anyone’s time.”
But time is a resource in short supply for those working to solve homelessness. And for those officials, AI has become a shorthand answer to problems the city is desperate to solve. The Standard has learned that at least two San Francisco homelessness nonprofits — Larkin Street Youth Services and Tipping Point Community, founded by Mayor Daniel Lurie — are testing AI tools that could make them more efficient.
Larkin Street CEO Sherilyn Adams said the nonprofit is partnering with an AI firm to determine which of its services are most effective. The software has created profiles based on the nonprofit’s client data and is analyzing which interventions worked best for each type of client.
“It’s just another tool in the toolbox,” Adams said. “It’s still a human-to-human interaction, and it’s still the case manager in making the ultimate determination.”
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Sources say Tipping Point also has an expansive AI project in the works, though the organization would not confirm this.
Los Angeles County officials have experimented with an AI program meant to identify at-risk people and families before they become homeless by analyzing the city’s client data. As of November 2024, roughly 86% of participants in that program had retained their housing (opens in new tab).
San Francisco’s chatbot for RV dwellers may be the first city-operated AI tool intended to directly interact with homeless people.
Some advocates are concerned that the bot is dehumanizing an inherently interpersonal line of social work. Many homeless people don’t have phones, and the causes of their homelessness are complex, often forcing social workers to harness their personal connections and experience to navigate the city’s tangled housing and shelter system.
Jennifer Friedenbach, executive director of the Coalition on Homelessness, said she worries that the AI software will be unable to navigate the dysfunction she encounters daily as part of her advocacy.
“These kinds of technological responses, when built on a broken system, just exacerbate the breaks,” Friedenbach said. “This is not a customer service person that is handling your order; it’s a lot more complex than that.”
The city says it has engaged in a months-long outreach process before the Nov. 1 ban on large vehicles. In May, outreach workers counted 501 such vehicles, whose owners qualified for a permit to temporarily stay in their vehicles — as long as they engage in the city’s housing process. Those who weren’t counted in the database (opens in new tab) are required to submit an application (opens in new tab).
Megan Rohrer, a policy director at Compass Family Services, thinks a chatbot could be useful as long as it’s paired with human outreach. He noted that an AI bot could simplify the complex and bureaucratic language of the permit process and parking ban.
“No one wants the homeless provider system to get more robotic. We always want it to be more human and loving,” Rohrer said. “But as long as it’s paired with choice, and people can make a phone call or stop by in person if they want, I’m in favor of it.”
Several RV dwellers confirmed to The Standard that outreach workers had informed them of the impending ban and permitting process, but most remain skeptical of the promises of permanent housing.
Many of those living in vehicles are monolingual Spanish speakers, and street advocates allege that the city’s communication has been mainly in English. The mayor’s office wouldn’t say whether the chatbot is being tested in Spanish.
For those who believe the city has failed them, it’s doubly hard for them to put their trust in a city-sponsored robot.
Isvela Cabrera, an immigrant from Central America, said her RV burned down last month, destroying the main requirement for the city’s permit process. Cabrera is now living in a friend’s trailer in the Bayview, but worries that she will be abandoned once the ban is enforced — without a vehicle and without a home.
“I feel like I have no rights,” Cabrera said in Spanish. “They always just leave me in the streets.”