It's a complicated issue with no easy answer.
Since 2009, the number of documented homeless has risen each year and 2016 could be no different.
"The numbers did go up. The question is why did the numbers go up," said Honolulu's Department of Community Services Director Gary Nakata.
Over the past year there has been a major uptick in the city's involvement with homeless outreach.
Programs like Housing First and the Mayor's Challenge to End Veteran Homelessness have gotten more than 400 people off the streets.
Service providers have also been hard at work. A program started by the state's tourism association in partnership with the Institute for Human Services housed another 384 people in Waikiki alone.
As more homeless connect with housing, Nakata says word is getting out.
"Some of the homeless in their own networks have been talking to each other saying you have to come out and be counted by government because they're actually doing really good things," said Nakata.
Last month, the city opened the first phase of its newest shelter on Sand Island.
"We have a total of 18 single units that are currently available and 11 of them are occupied," said Institute for Human Services Director Connie Mitchell.
Although the city has seen some success, Mayor Kirk Caldwell says one of the biggest challenges is finding properties to purchase and convert into housing.
He says often the city is simply outbid.
"We found a property on Kapahulu. Four units, two bedrooms each. We wanted that one. Twenty offers were made and we didn't get it."
Meantime, the city is preparing for next month's homeless count -- and hoping for a clear cut understanding of the new numbers.
"The main thing is we need to ask people, 'Have you been counted before have you not been counted before?' It would be really interesting to find out those that have not been counted before why are you being counted now," said Nakata.