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Not much is known about Harry's early life, although it was stated in Kingsman: The Golden Circle that he wanted to become a lepidopterist, but instead chose to become an officer in the British Army. After serving in the military for some time, he was recruited into Kingsman.
Part of Harry's training included him in his and his fellow trainees' sleeping quarters filling up with a load of water and their response to it (which they supposedly completed successfully) and also choosing a puppy and caring for it during their training (Harry's being a Cairn Terrier he named Mr. Pickle). Sometime into his training, Harry was made to shoot Mr. Pickle (though unknown to him the bullet was actually a blank as part of their training). Harry was given the title of Galahad following this and continued to care for Mr. Pickle until the latter died of Pancreatitis.
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