There have been many changes at St Joseph's Primary School Merewether over the past century but at least one tradition has remained.
Every few decades, one of Henry Leonard's ancestors has enrolled in the school.
When the 5-year-old starts kindergarten today, he will become the fifth generation in his family to attend St Joseph's.
His mother Rachael started her own school journey there nearly 30 years ago and made lifelong friends.
"I only have fond memories of my time there," the 1997 school captain said.
Before her, Mrs Leonard's mother Susan Howells attended St Joseph's Merewether in the 1960s.
"I remember lots of happy childhood memories," Ms Howells said.
"I lived locally so sometimes I'd go home for lunch or Mum would bring sandwiches over and our family dog would come to pick us up of an afternoon and walk us home."
Ms Howells' parents Kevin and Mary O'Connor attended the school in the 1930s, following on from Henry's great-great-grandfather David O'Connor, the one responsible for starting the family tradition.
Ms Howells said she was excited when she heard the tradition would continue with Henry.
Although, considering even his paternal grandmother Joanne Leonard was also a student of the school, it was likely Henry would end up there too.
"I started kindergarten here in 1949 ... it was quite different then," she said, adding that she had not returned to the school since she was a student.
"All the teachers were nuns and it was quite strict. It just looks totally different."
Henry's mother said that while the family's history at the school was a convincing factor, she and her husband Matthew still felt like St Joseph's would be a great fit for him, and later on, his twin brothers.
"We've been attending the playgroup of a Thursday since the boys were little so it just feels like a natural progression," she said.
"I have mixed emotions.
"It's the end of the baby era but I'm excited for the future for him.
"He's very excited. I'm not sure what will happen when he realises it's five days a week but he's very excited to be starting big school.
"I just hope he settles in and finds a nice group of friends and enjoys what's on offer to him."
While Henry is sure to make new friends during his time at St Joseph's, it's clear he already has a loving support network around him in his family.
He is looking forward to using the school's new playground and feeding the classroom "fishy".
He's already got a future career in mind too. He'd like to be a ninja.
