Apollo Justice: Ace Attorney Trilogy

There are four different dialogue segments About Apollo's unfortunate working conditions that you need to hear across Dual Destines and Spirit of Justice to unlock this achievement. You can check which ones you still need in the Accolades section of the museum on the main menu:

Dual Destinies Episode 5 - Turnabout for Tomorrow - At the very start of the Episode, once the initial dialogue is over, ask Trucy "What To Do".

Dual Destinies Special Episode - Turnabout Reclaimed - During the Day 2 investigation, just after examining Orla's food, go back to the Wright Anything Agency and Present Apollo with The Whistle, and then The Fish for 2 of the dialogues. If you missed this the fastest checkpoint to load up is "The Show Stage".

Spirit of Justice Episode 5 - Turnabout Revolution - This one is unmissable if you're playing through normally and should come up when you're questioning Sergeant Buff and they hand you a broom during the Day 1 Investigation.

When I was playing through the Achievement didn't unlock properly after talking with Sergeant Buff, even though it showed on the accolades that I had gotten all 4. Loading up Turnabout Reclaimed and presenting Apollo with the whistle again got the achievement to pop.