Eden Hasson had been surfing for most of the afternoon at Samurai Beach, near Newcastle, when he went to catch one more wave.
The 10-year-old, who was with friends and family, paddled at the northern end of the beach and took off on a left-hander.
He thought he saw a dark shape nearby, but continued on as his father Chris - a lifetime surfer - took photos from the shore.
The dark shape also caught the eye of Mr Hasson, a real estate agent, as he stood on rocks at the northern headland. He continued snapping away as Eden rode the wave into the beach and started paddling out again.
Then he zoomed into the photograph and saw it - the head of a 2.5-metre great white shark in the face of a wave, with Eden surfing next to it. He immediately called Eden back to the shore.
"Check its mouth," Mr Hasson wrote shortly afterwards on Facebook. "It's rolled over having a good look at his yummy yellow new wetsuit."
The extraordinary photograph was shot on Tuesday night as Eden and four other surfers were enjoying the last of the waves.
Mr Hasson told Fairfax Media that Eden was in the water with his sister Olivia and a friend when a storm approached, prompting Olivia and the friend to paddle into shore.
Five people were left in the water, including the "talented" and "competitive" young surfer.
"I took the camera onto the rocks and started taking photos when I noticed a dark shape," Mr Hasson said. "I was just about to call everyone in when Eden took off on the wave in the picture and I took a number of shots.
"Eden rode the wave to the beach. I quickly zoomed in on the second photo and was shocked when I saw the image. Eden was half way out and I called everyone in. I showed them the photo and everyone was in awe laughing.
"One of the surfers said just before the wave a large school of mullet arrived."
Eden said he also saw the shape, and felt something beneath the water, but didn't realise it was a great white shark.
"When I took off I thought I saw something and when I went to do the first snap off the top I hit something and I thought it was seaweed," he said. "Then when [Dad] called me in I thought it must be a shark because there was a big school of fish."
The experience hasn't scared the Hassons or other locals who surf on the Tomaree Peninsula - they have always known they were sharing the water with sharks.
"I've always taught the children about respecting the ocean and that sharks are to be respected, not feared," Mr Hasson said.
"Eden is not deterred and has already paddled out for a surf the next day. He loves surfing and the ocean. It's only created a greater awareness."
Mr Hasson said he has surfed the area for 30 years and sharks "have always been there, and always will be".
"I've seen quite a few in that time and simply paddle in if we see one and regroup for another beach or day," he said.
Marine ecologist and shark expert Danny Bucher said he believed the shark may have been startled by Eden.
"They will roll after biting into, say, a whale carcass in order to tear off pieces," Dr Bucher said.
"Rolling on approach would take the surfer out of the shark's field of vision, so I don't interpret this move as particularly aggressive or predatory.
"Quite the opposite, it may have been startled by the rapid approach of the board and has broken the surface in a rapid change of direction away from the surfer."