NSW Environment Minister James Griffin said the release on Wonnarua Country was the second large-scale release of the endangered honeyeaters undertaken in NSW.
"The regent honeyeater used to flock in its thousands from Queensland to South Australia, but now there are only around 300 birds left in the wild," he said in a statement on Sunday.
"We're releasing conservation-bred birds to boost numbers in the wild as part of a national effort to save this critically endangered species.
"We recently learnt that wild regent honeyeaters are losing their song culture because there are fewer older birds for young regent honeyeaters to learn from."
Mr Griffin said the ability for the honeyeater to sing and call was vital to attracting a mate and the introduction of the Taronga Zoo-bred birds would give the wild birds the chance to learn their songs again, find mates and ensure survival into the future.
In 2021, 58 regent honeyeaters were released in the Lower Hunter Valley, and breeding activity was documented along with assimilation of zoo-bred birds into wild flocks.
Mindaribba Local Aboriginal Land Council CEO Tara Dever said the release on Mindaribba land reflected the deep relationship between the birds and the country at the foot of Mt Tomalpin.
"While conditions need to be just right to ensure the birds have enough food and shelter, the deep connection between First Nations People and this land has assisted with the success of the release," Ms Dever said
The breeding program is led by Taronga Conservation Society Australia, BirdLife Australia and the NSW government's $175 million Saving our Species program.
Taronga Conservation Society Australia wildlife conservation officer Monique Van Sluys said almost 600 regent honeyeaters have been bred at Taronga Zoo Sydney and Taronga Western Plains Zoo since 2000.
"Over the past 20 years, Taronga has refined its approach to conservation breeding and increased our understanding of this beautiful and rare species," Ms Sluys said.
"Juvenile zoo-bred regent honeyeaters are now housed in aviaries with wild adult birds to be exposed to their wild regent honeyeaters' song prior to release. This crucial step allows the birds to learn and refine their distinctive song."
BirdLife Australia's NSW Woodland Bird Program manager Mick Roderick said around 39 birds will be monitored for up to 10 weeks by BirdLife Australia.
"Monitoring will involve a small radio-tracking crew, following transmitter signals and recording individual bird locations and behaviour to understand survival, breeding attempts and dispersal patterns," Mr Roderick said.
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