Later this month, the former deputy principal of Pamapuria School, James Parker, 37, will be sentenced on 49 charges of sexually abusing boys. Police say more charges are pending.
Mr Tailby, who was born and raised in the town of 5500, said that when the news broke about Parker, suppression orders meant the school was hamstrung in the way it could deal with the issue.
"The whole thing was everyone knew, but no one could talk about it.
"All we were able to do at that point was send out newsletters, talk at assemblies: 'If you're having difficulties these are the channels, these are the places to go and get help'.
"It was a case of constantly putting out the message that it's okay to come and talk to someone."
The school faced the challenge of protecting privacy.
"We can't be sitting there isolating or identifying these students. These students do not want to be identified so any support we might be able to offer, we have to be very careful that we're not seen as ... putting big red flags over their heads," he said.
"I'm very conscious of not actually stigmatising young people here and that they are allowed to make their own choices about their life."
It had been a weary load for many involved but the hope was students would have a normal and successful high school career.
He believed the people of the town were generous and resilient. To be judged on the actions of a few would be unfair.
Iwi leader Haami Piripi, of Te Rarawa, said he knew the men in the cases. From his own knowledge, their backgrounds didn't extend deep into the town's past.
"They are definitely seen as external agents. We don't see the inner sanctum, integrity of our community has been breached so there's plenty of room for us to rebound and rebuild and re-energise our community with an air of confidence."
Mark Dalzell, acting Detective Sergeant in charge of child protection, has worked in the town for 15 years and said there had never been two cases at about the same time involving "mass allegations".
"In some ways it's confirmation the community in Kaitaia won't stand for this behaviour and they have the confidence to call us. If it wasn't for the information we get from the community we wouldn't get on to these guys - simple as that."