make sure you fly towards the azura on the first part of the mission as it starts and it should work.
also this was retroactive. if you have already flown through the hole, when they first updated the game a couple of weeks ago you would have gotten the accolade as you logged in, so you might already have it.
_I_ found (your experience might differ) that you have to fly through it from the backside towards the azura and not out into open space from the azura side. I just did it with all my characters on Holodeck and it worked everytime flying towards the azura, so give that a try.