During the prolonged siege of Troy, the young prince Troilus seeks the affection of Cressida while the Greek and Trojan armies engage in a stalemate of philosophical and physical conflict. Troilus navigates the complexities of courtly love and the disillusionment of war, while Cressida faces the precarious reality of being a woman caught between warring factions. The narrative framework utilizes a blend of high-flown rhetoric and cynical realism to examine the breakdown of traditional heroic ideals. Characters are constrained by the rigid expectations of honor, duty, and the inevitable decay of their societal structures as the conflict drags toward an inconclusive end.

Discussion often centers on the play's refusal to fit neatly into the categories of comedy or tragedy, leading many to label it a problem play. Readers frequently highlight the stark contrast between the romantic aspirations of the protagonists and the cynical, often grotesque, depictions of the warriors on both sides. Critics often examine how the text deconstructs the mythic status of figures like Achilles and Ajax to reveal human pettiness and moral ambiguity. The work is noted for its linguistic density and its challenging, often uncomfortable, perspective on the nature of honor and loyalty. Many find the play's lack of a traditional resolution to be a deliberate stylistic choice that mirrors the chaotic and senseless nature of the conflict it depicts.