Pterostylis woollsii, commonly known as the long-tailed rustyhood, is a plant in the orchid family Orchidaceae and is endemic to eastern Australia.

It has a rosette of leaves at its base and up to six transparent flowers which have unusually long tips on their lateral sepals and a reddish-brown, insect-like labellum.

[1] Fitzgerald gave the specific epithet (woollsii) "after my friend, Dr. Woolls, who has contributed so largely to the knowledge of Botany in New South Wales, and who kindly sent me specimens discovered by him growing in the neighbourhood of Richmond".

[6] The long-tailed rustyhood has a widespread but disjunct distribution in New South Wales where it grows in forest in grassy or rocky places.

[3][4][5] Pterostylis woollsii is classified as "endangered" in Victoria under the Victorian Government Flora and Fauna Guarantee Act 1988.