Yet that does not appear to deter Mr. Phillips, who is trying to persuade people whose plight he once shared to break out of this life. “We come out here, we try to get them into the shelter, cleaned up,” Mr. Phillips said. “At that point, we’ll try to do an intervention: ‘Hey, you want to go to detox? By the way, we have an outpatient program for alcohol and drugs. Can I sign you up?’ ”

While punitive laws have drawn criticism from federal officials, they are applauded here by some advocates of the homeless. “A lot of people say these laws don’t work,” said Kimo Carvalho, the director of community relations with the Institute for Human Services. “But as a service provider, we advocated for these laws because our homeless outreach teams need to motivate clients to take action.”

Two years ago, the Hawaii Lodging and Tourism Association gave $500,000 to the Institute for Human Services on a promise from the institute that it could cut the homeless population in Waikiki in half. The money went to pay for teams like the one Mr. Phillips was leading, a shuttle to take people to a shelter for a shower, clean clothes and food, and the airline relocation program. “This is our economic engine. We absolutely had to do this,” said Mr. Szigeti, the head of the Hawaii Tourism Authority, who was the president of the lodging and tourism association at the time.

There were 559 men and women living on the streets of Waikiki and Chinatown when the program began in November 2014. As of early March, that population had been slashed by 392, Mr. Carvalho said: 219 had been placed in temporary or permanent housing, and another 173 had been flown out.

Still, enforcement is a fraught subject in Hawaii, whose allure is built in no small part on marketing itself to the world as the Aloha State, with a welcoming atmosphere. Mr. Caldwell recoils at the use of words like “sweep” and “confiscation.” Leland Cadoy, a police corporal walking the streets of Waikiki with a reporter, kindly addressed every homeless person he saw, and spoke only of “R.C.P.s.”

“Residentially challenged people,” he said, when asked about the acronym. “You call someone homeless, it sounds derogatory.”

Even as he applauded the changes in Waikiki, David Ige, the governor, said the crackdown was not the answer to the homeless crisis that has become such a part of life here. He said that what Honolulu needed was affordable housing, a goal that has stubbornly eluded this island.

“Homelessness has reached every community in the island — in areas where you didn’t see them five years ago,” he said. “If you are just enforcing and moving people from location to location you are not really reducing or solving the problem. It’s just making it someone else’s problems. It’s not like they can leave the state.”