Dieppe reminds us the West values the lives of its troops and illustrates other fundamentals about Westerners, yet the August 1942 raid remains controversial and filled with ambiguity. This article does not seek to clarify each puzzle but to draw attention to some enduring facts of war. Many of the quandaries and predicaments the Allies experienced before, during, and after the raid are not unique to Operation Jubilee; thus it remains relevant for today’s military planning, combined joint operations, and postdisaster accountability. Ten factors for the operation’s failure are considered. Moreover, it was a combined joint operation, so everyone could blame everyone else. Discounting such labyrinths, Operation Jubilee is still a rewarding source of reflection for military planners and practitioners.