Pony, as named by Mr. Jingles, was first encountered in a stable in the town of Essembra. Pony had an immediate bond with Mr. Jingles, and at times appeared to show some semblance of intelligence. Not wanting to part with Pony, Mr. Jingles opted to steal his new friend. As they exited the stables, Galadrathril tossed 20 gold pieces at Pony's then owner, Chesduk II of the Watchful Eye inn, as payment for the pony. Chesduk shouted after the fleeing party that the pony was not for sale.

While on the road, the party was attacked by bandits, one of whom suggested Pony might make an excellent meal. During this encounter, Pony exhibited some basic combat skills, but seemed less equipped at leaping over obstacles.

Days later, in Chandlerscross, Emmit encountered a human ranger searching for a pony and a horse thief matching Mr. Jingles' description. The ranger indicated that he had been hired to seek out the alleged thief and return the stolen "pet" to its rightful owner.