Begging appears to be on the rise, with social services noticing a greater diversity of people on the streets.
And the act of giving money to those doing it tough was highlighted after images of Prime Minister Jacinda Ardern appearing to give cash to a person in Wellington's CBD at the weekend emerged on social media.
There remains an unprecedented demand for emergency and transitional accommodation, with the latest figures from the Ministry of Social Development showing 26,664 people were on the social housing register - up nearly 9 percent year on year.
In addition, the Auckland City Mission said it gave out 64,000 food parcels in the year to July - equating to about 3 million meals.
Auckland City Mission health and social services general manager Jacqui Dillon said every person had a reason as to why they were on the street asking for money.
Dillon told AM people should feel comfortable giving money if they wished.
"I think the first thing to think about is what you're comfortable doing in terms of engagement," she said.
"Sometimes it's not just about the money - sometimes it's about that human desire to be seen, to be heard, be connected with."
Dillon said giving money to people in need would help some but it was on a case-by-case basis.
"I'd encourage people to engage: find out what their story is - for some, it is about a need for a hand up. For others, it might be more appropriate to encourage them to go along and engage with one of the services or call up one of the services and say, 'Hey, I'm really concerned about the fellow down on Lambton Quay' or wherever else."
While the exact number of rough sleepers or people in need in the likes of Auckland was unknown, a University of Otago analysis of 2018 Census data showed nearly 500 people did not have a shelter - but this was thought to be an underestimate.
Wellington City Missioner Murray Edridge people were doing life harder with availability and access to quality housing being a major issue.
He urged New Zealanders to treat people in need with care and compassion.
Edridge said people should trust their gut over whether they give money to those people or not.
"Is it appropriate to give people things? Well, it depends on [the] circumstance and maybe it's better to offer someone a cup of coffee but it is about creating [a] connection with people we don't know their circumstances - we don't understand why they're there," he told AM.
"Don't put yourself at risk but engage with people and just see where it goes, and you'll come to a feeling about what's appropriate to do in the circumstances.
"In [a] circumstance, if it's more appropriate - and you judge it to be more appropriate - to give someone some cash, that's OK."
Alongside that, people could also donate to organisations like city missions which worked to support people in need.