The event, St Vincent de Paul's biggest fundraiser, sees business and community leaders spending a night outdoors with nothing more than a sleeping bag, a piece of cardboard for a mattress and another folded piece providing some rudimentary shelter.

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Vinnies' South region director Emily Gray said the night usually starts out with lots of friendly laughter, but things change in the wee hours.

"Certainly around three in the morning when it starts to get really cold, and a lot of them haven't been to sleep or they're getting up because it's cold, the reality what it's like for our homeless community really sinks in," Ms Gray said.

"That's why it's not just about raising money. It's about getting that connection and giving that empathy for what it's like for people who don't have a home."

Ms Gray said Vinnies was hoping to make around $9 million across Australia and more than $100,000 from the Illawarra sleepout.

That money would go to fund the services delivered at the Coniston hub, like meals, showers and accommodation.

Flagstaff CEO Roy Rogers was taking part in his 11^th straight Illawarra sleepout after convincing St Vinnies they should look to stage them in regional areas.

He said the first sleepout was in MacCabe Park where the wind picked up in the middle of the night and blew all the cardboard shelters away.

In those 11 years, he's become quite familiar with the freezing cold at 3am, where his nose is coated in frost because it's the only thing sticking out of his sleeping bag.

He said it was in those moments when you really started to think about the homeless people who didn't know where they would be sleeping from one night to the next.

"A lot of people are living on a knife's edge," Mr Rogers said.

"It doesn't take much to make a person homeless. It could be a marriage break-up, it could be a mental illness, it could be mortgage stress.

"Something happens in a person's life and, the next thing you know, the whole thing's disappeared and they homeless and they haven't got any way to go.

"We have too many people living like that in a great country. We have way too many people who are living on the streets and haven't got a roof over their head and we need to be able to rectify that."

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