1. Richard Shelton initially appears as an inexperienced young man who takes things at face value, unaware of the complex realities of his world. How does he become more enlightened and mature?

2. Dick starts out as a male chauvinist who dismisses women. How does he come to respect and eventually love Joanna Sedley?

3. To what extent does Joanna embody a liberated heroine, and to what extent is she the typical romantic fiction heroine who needs rescuing by the hero?

4. In books 1 and 2, Joanna Sedley plays a significant role; in the remaining three books, she appears only briefly, and Stevenson introduces Alicia Risingham as a potential rival for Dick's affection. Is it a mistake to remove Joanna after book 2?

5. In Shakespeare's plays, popular mythology, and films like the two versions of The Tower of London (1939 and 1961), Richard III is depicted as a monstrous villain. Stevenson's Richard of Gloucester, who will become Richard III, is portrayed as a younger man not yet fully corrupt, who befriends and aids the hero. What evidence suggests Richard has the potential for evil, and why is it wise for Dick not to stay his follower?

6. In The Black Arrow, amid a civil war, loyalties and alliances shift. How does Dick realize that his supposed protector, Sir Daniel Brackley, has betrayed him? By changing sides, does Dick become a traitor or find new freedom? Are the outlaws subversive criminals, terrorists, or freedom fighters? Why do Richard and his new protector, Richard of Gloucester, become estranged? What does this estrangement reveal about their characters? Is either the York or Lancaster side superior?

7. Are there any similarities between the political conflicts during the Wars of the Roses in The Black Arrow and today's quarreling factions?

8. Does the novel's archaic prose style and diction enhance or hinder the narrative? Can it be justified for the sake of realism, or is it merely an artifice?