Hi Aaron I have compared your Caladenia photos with mine and based on the flowering time: May-July and the red on the inside of the column, I think your Caladenias are Caladenia picta. Caladenia catenata is less common in the region, less coastal, with a green front column and also flowers in August - September. I have previously had my Caladenia picta (they are the same as yours) confirmed by Alan Stephenson and the Sydney herbarium. I would imagine flowering time to have been an important isolating mechanism in the evolutionary separation of these two species. NIck
Flowering time is conclusive for C.picta, recently reclassified as Petacochilus pictus. Aaron, do an enlargement of the centre of the flower to confirm the column is red on the front.
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