Only two months ago, the council approved a last minute bid by the airline to start a passenger link between Masterton and Auckland - replacing the defunct Eagle Air service - and turning down a proposal by rival airline Air Chathams in the process.
The decision to back the Vincent Aviation bid came after the airline's managing director, Peter Vincent, spoke to all councillors at a closed door meeting and despite knowing that Vincent Aviation's Australian arm had gone into receivership.
Now, ANCL Investments Ltd has filed an application in the High Court at Wellington to liquidate the airline.
Failure by Vincent Aviation to start the service would be the latest in a long line of on-off attempts to sustain a successful passenger air service from Masterton.
A bird in the hand?