Meanwhile, Henry's romance with Miss Stapleton hits a rough patch. Henry, going out to meet her, excuses Watson of his duties as bodyguard, lest the doctor turn into a chaperone as well. All the same, Watson trails the baronet and sees him walking with Miss Stapleton. As Henry bends in for a kiss, Stapleton arrives on the scene, yelling and carrying on inexplicably. As the Stapletons depart, Watson reveals himself to Henry, who wonders whether Stapleton might be crazy. He things himself a worthy match for Miss Stapleton, though he admits that on this occasion she refused to talk of love and only offered mysterious warnings. Later that day, Stapleton meets Sir Henry at home to apologize for his over- protective nature, and invites him to dinner next Friday.
Meanwhile, Watson and Henry's stakeout takes two nights of vigilance. On the second night, the two hear Barrymore and follow him to his window. Watson watches as Sir Henry confronts him. Shocked and bewildered, the butler tries to furnish an excuse, but Sir Henry insists on the truth. As Barrymore waffles, protesting, Watson goes to the window, figuring that another person out on the moor must be matching Barrymore's signal. Sure enough, a light shows up across the moor, but the butler refuses to talk, even at the expense of his job. Suddenly, Mrs. Barrymore arrives and explains everything. The light on the moor is a signal from the escaped convict, who turns out to be her brother. The Barrymores have been feeding and clothing the man so he does not starve out on the moor. Excusing the Barrymores, Henry and Watson determine to go out and capture the convict, so as to protect the community. On their way toward the light, though, the pair hears the loud moaning of a wolf and wonders whether they should continue their adventure. Watson even admits that the locals suspect the braying to be the call of the Hound of the Baskervilles.
Frightened but determined, Sir Henry insists they proceed. When the pair finally reaches the flickering candlelight, they spy a small crevice in some rocks where candle and convict are carefully hidden. The convict turns out to be all the two might have expected: haggard, unkempt, and animal-like. When Watson moves in for the kill, though, the man manages to escape. Just then, as they make their way home, Watson catches sight of a lone figure, silhouetted against the moor. But as suddenly as the tall, mysterious figure appeared, the figure is gone.
There are several clues presented in Chapter VIII but little analysis: we learn of Stapleton's deep passions and Watson reiterates Miss Stapleton's exotic beauty. At the same time, the novel moves forward when the subplot of the escaped convict is addressed, and we are left to wonder how the convict figures into the broader mystery.
At the end of the chapter, when Watson leaves it to Holmes to figure things out, he is also leaving it to us to come up with our own theories. Instead of involving Holmes, who is could surely figure this all out quickly, Doyle lets Watson tell the story, thus leaving the clues disconnected and the legend intact. Though Watson seems pleased that his master entrusted him with so much responsibility, it will turn out that Holmes did not trust him at all, and the doctor will end up looking more like a fool.
In this section, we also meet Mr. Frankland, who serves as a much-needed dose of comic relief in an otherwise grim tale. He talks of the locals burning him in effigy or carrying him through the streets, depending on whether he has done them a service or a disservice on that particular day. At the same time, the character of Frankland satirizes the idea of entitlement and hierarchy, although it is not clear which side he is on. Frankland's gratuitous lawsuits, aimed at protecting what he sees as his rights, suggest that Doyle has a humorous take on this character's actions and opinions. But we are unsure whether Doyle is satirizing all entitlement, or a middle- and lower-class assumption of the rights of the nobility.