The Dwarves send Bilbo into the secret passage first, though Balin comes with him a little bit of the way. Bilbo steals a cup from the treasure horde; Smaug becomes enraged when he awakens. Bilbo again goes down to the dragon's chamber, though this time he is caught by Smaug, who was pretending to be asleep. The hobbit manages to escape and rejoin the dwarves, worried that one of his riddles has led the dragon to suspect the intruder hails from Lake-town. Bilbo convinces his comrades to close the door to the secret passage, just in time to protect them from Smaug’s attack on the side of the mountain.
The dark passage into the mountain stands open before the Company. Thorin nominates Bilbo to go inside first. Bilbo enters, puts on the ring, and proceeds down the passage into Smaug’s lair. There, he sees the dragon asleep on piles of treasure. Bilbo is horribly afraid, but he works up the nerve to take a single golden cup from one of the piles. He rushes back up to the dwarves, who marvel over the cup.
Bilbo’s theft does not go unnoticed by Smaug, who takes careful account of the treasure. When he awakens, he is enraged to discover the cup is missing. He flies around the mountain breathing blasts of flame, and devours the ponies that belonged to the Company. Meanwhile, the dwarves and Bilbo huddle inside the secret passage, terrified. After a while, Smaug returns to his den and falls asleep. Bilbo works up the nerve to return to the dragon’s lair, only to discover that Smaug was just pretending to be asleep.
Although he cannot see Bilbo because of the ring, Smaug smells him and greets him mockingly. Bilbo answers Smaug only in riddles, which amuses the dragon enough to quell his anger. Cleverly, Bilbo flatters Smaug into displaying his underbelly, revealing an open patch in Smaug’s "diamond waistcoat" above his left breast.
Bilbo rushes back up the passage, just outrunning the dragon’s angry flames. He tells the dwarves all that he has learned while a thrush sits nearby and seems to listen. They hear the roar of the dragon once more and close the secret passage just before an avalanche comes down upon it, and they become trapped inside the mountain.
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