This quest will appear in your journal after completing the quest "What the Devil!" as long as you have not yet recruited two officers - Lucy and Padre - into your crew.
Edward must bolster his crew with more officers before he can face Maynard and his armada.
Hints:
You do not need to complete all quests for each of the officers. In Lucy's case, it is enough to complete the quest "The One With the Gun", while for Padre, completing the quest "Loyalty, Discipline, and Courage" is sufficient.
Once you meet these criteria, this quest will become history, and the quest "It's a Start" will appear in your journal.
