Many years pass since Pinocchio has abandoned Emma, and he has adopted the name August Wayne Booth. August catches Neal in Portland after he and Emma successfully pull off a heist of stolen watches. He tells Neal that if he truly cares for Emma, he will leave her to her destiny and not allow her to be caught up in his life. At first, Neal refuses, as he truly loves Emma. August states that Neal does not believe him, but he will show him something that will change his mind. August goes to the back of his motorcycle where there is a wooden box. He opens it, and reveals the contents for Neal to see. Inside the case is August's typewriter and a piece of paper, on which he had typed, "I know you're Baelfire". The revelation that someone else knows his secret shakes him to the core, and Neal follows August's request. He runs off and frames Emma for the theft. ("Tallahassee", "Manhattan")
After a few months, August meets up with Neal in Vancouver. Neal is torn over leaving Emma and wants to know she is all right. August only states that she is sentenced to eleven months in jail and is in a minimum security prison in Phoenix. Though Neal wants to go to her, but August stiffly reminds him of their deal. Since he can't visit her, Neal wants to give Emma the yellow bug and the money he got from the stolen watches. August reluctantly agrees to carry out the task for him. Lastly, Neal asks to be informed if something changes in Emma's life so he can be with her, so August promises to send a postcard. Later, from Phuket, Thailand, August mails Emma the car keys, but doesn't include the money. ("Tallahassee")
At some point during his time in Phucket, August meets the Apprentice, who guides him into learning more about the storybook. ("Operation Mongoose Part 1")
One morning, during October 2011, August awakens at eight-fifteen to a shooting pain in his leg as he begins reverting into wood. He goes to a Hong Kong-based hospital for a remedy, but the doctor cannot see that his leg is wooden. In his desperation, August stabs himself in the leg to prove it, but instead frightens the doctor, who calls security. After eluding capture, he meets a man who claims that, for the right price, a healer called the "Dragon" can help him. August goes to a clinic where a female patient, Tamara, is called into the Dragon's office. When she drops her cellphone, August hands it back. Moments later, August has his turn with the Dragon, who reveals knowledge about his true identity as Pinocchio. As payment for the cure, the Dragon takes a whale-shaped necklace; something August's father used to animate him into a puppet. Secondly, August must give ten-thousand U.S. dollars, which he later steals from Tamara. The Dragon gives the cure as promised, but he warns that only August can truly heal himself. When he is confronted by Tamara, August runs, until searing pain from leg causes him to collapse, to which she retrieves the Dragon's cure. Before leaving, she bitterly remarks that he deserves whatever condition he has. A few days later, he returns to ask the Dragon to cure him again, but finds the man dead. In the Dragon's belongings, August finds research about the storybook Author and takes it with him. Realizing he cannot outrun his fate, August decides to convince Emma to believe in the curse and break it, in the hopes doing so will reverse his wooden state. Before going to Storybrooke, he goes to Neal, who now resides in New York City, to fill him in on his plans. ("Selfless, Brave and True", "Poor Unfortunate Soul")
Some time later, August rides into Storybrooke on his motorcycle, where he meets Emma and Henry for the first time. He asks them where he can find a place to stay, and Emma directs him to Granny's inn. Before he drives off, she asks him what he said his name was, to which he replies that he never gave it. The next morning, he is repairing his motorbike in front of the mayor's house, and Henry comes out to talk to him. August deflects most of the boy's questions and drives off, but not before Regina spots him first. She asks Henry who that is, but her son does not answer her.
Later, at Regina's request to learn more about this "stranger," Emma questions him at Granny's Diner, while he is drinking coffee. They have several minutes of a back and forth banter, in which he taunts her about the wooden box he carries around, but he eventually agrees to show her what is inside if she will let him buy her a drink sometime. She agrees to this, and he opens the box to reveal a typewriter. Upon further inquiry, he reveals that he is a writer and that he came to Storybrooke because it was full of inspiration. As he gets up to leave, Emma asks him about the drink he promised her. He grins and says, "Sometime," then walks out the door. ("7:15 A.M.")
After Henry's castle is destroyed, August takes the storybook from its hiding place and brings it back to his room at the bed and breakfast. ("Fruit of the Poisonous Tree")
He and Emma run into each other at Granny's Diner. August asks Emma out for that drink he promised her and says he knows a good watering hole. At first, she is reluctant, but after some encouragement from Granny and August telling her what his name was, she agrees, and he takes her to a "wishing well" that, according to legend, has magical water that could restore a lost item to a person.
Secretly, August begins "repairing" Henry's storybook, adding the story of Pinocchio to it. The next day, Emma finds the storybook on the ground as she is brushing leaves off of her car. August is watching her from around the corner as she picks it up, hinting that he might have placed it there on purpose. ("What Happened to Frederick")
A few days later, he is talking to Ruby at Granny's Diner, telling her about his adventures while travelling. He tells her about visiting Nepal and how their temples were infested with lemurs. When Ruby inquires about his adventures further, her grandmother calls her over impatiently. August is silent as Ruby confronts her grandmother and quits the diner. ("Red-Handed")
Many days later, after Ruby and her grandmother reconcile, August finds Henry poring over his storybook. They have a quick discussion about Mary Margaret's arrest over Kathryn's disappearance, and August reveals that the storybook's tales just might be true. This excites Henry, and the mysterious writer says that he has come back to Storybrooke to help Emma believe in Operation Cobra. When Henry tells him that he wants to find proof of Mary Margaret's innocence, August implies that he should look in the book for answers, and leaves the diner. ("Heart of Darkness")
While sitting with Emma at a diner table, August expresses a desire to ask her out again, but he knows it's not the best time since she is working on Mary Margaret's case. Still, he offers to buy her a drink, which Ruby goes to fetch. Noticing that Emma is staring at Regina, August asks what she plans on doing. Emma wants to give her a piece of her mind, but it has not been working out lately. As a new approach, August gives her advice that he got from his travels in Pamplona, "Don't let them see you coming." He then gets up, leaves money to pay for Emma's drink and leaves.
August converses with Emma about Kathryn and tells her to go over the case again starting from the point of view she has now, a cover up by Regina. They go back to the scene where Ruby found Kathryn's heart. Emma finds a chipped piece of what seems to be a shovel. Later that night August and Emma, with the help of Henry, enter Mayor Mills's garage and find a shovel with a missing section that fits the chipped piece they found earlier. The next day, Emma tries to confront Regina about it, but the shovel had been replaced with a new one. Emma later blames August for telling Regina about the shovel, and, when he denies her accusation, she suspects he is lying. However, after finding a "bug" spying device in a vase left for her by Sidney, Emma finds August and apologizes. They are interrupted by Ruby's scream, who tells them, "She's in the alley." Upon further investigation, they find Kathryn alive in the alley. ("The Stable Boy")
The next day, in his inn room, August wakes up with intense pain in his left leg and falls off the bed. When the phone rings, he drags himself to the desk to pick up the call. With Henry on the line, August tells him their plan is taking too long and it needs to be accelerated. With his own intentions of searching for Mr. Gold's dagger, he tricks Henry into sneaking into the pawnshop as a decoy. Henry, believing this is part of Operation Cobra, does as August asks. Sneaking through the backdoor, August snoops around until he is caught by Mr. Gold and feigns looking for a map. With the murder charges against Mary Margaret dropped, a party is held in her apartment to welcome her back. There, Henry inquiries about the pawnshop search, but August states it was unsuccessful. Later, August seeks guidance from Mother Superior about reuniting with his father, who he parted with on bad terms. A suspicious Mr. Gold interrogates the nun about what August told her, and when she discloses the reason, he mistakenly believes the man is his lost son Baelfire. That evening, Mr. Gold apologizes to August for abandoning him and asks for forgiveness. August plays along, eventually asking him for the dagger, which the latter gives willingly. However, when August attempts to use it against him, Mr. Gold realizes he is not Baelfire. Under duress, August confesses he is from the Enchanted Forest, and his sickness can only be cured with magic. Believing him to be useful, Mr. Gold allows him to live in order to get Emma to believe in magic. ("The Return")
August tries to get Emma to believe she is the savior by taking her to the place outside of where she was abandoned as a baby. He confesses he was the seven-year-old boy who found her, and he shows her the tree they both came through from the Enchanted Forest. He reveals details about Emma only she herself would know about, such as the blanket she was wrapped in as an infant. When August admits he is Pinocchio, she does not believe him, so he tries showing her his wooden leg. However, Emma's disbelief in magic causes her to see nothing amiss. As they argue, he becomes increasingly upset Emma doesn't want to believe she is the townspeople's only hope. She refuses to be responsible for everyone else's happiness, and then leaves. Failing to help Emma, August accepts his inevitable fate of turning back into wood. With little time left, he decides to spend it with his father. While Marco is in his workshop fixing the clock, August tells him how to repair it while also asking to be his Apprentice. Marco states he cannot pay him, but August is fine with that. ("The Stranger")
Henry rushes to see August Booth and tells him about Emma's desire to leave. August tells him that he tried to make Emma believe in magic, but he failed and is paying the price. He shows him his now wooden arm, which he calls the "unvarnished truth", and Henry realizes that August is Pinocchio. He says he is changing back, because he has not been a good boy. August explains that it is hard for him to continue moving and soon it will be hard to breathe, and he just wants to spend his last bit of time with Marco, his father. He tells Henry that it is up to him to continue Operation Cobra. ("An Apple Red as Blood")
After Henry falls into a coma from taking a bite of the apple turnover
, which Regina poisoned, Emma finally truly believes in the curse. She goes to August's room, hoping he can help her cure Henry. August cannot open the door and Emma enters, seeing August lying on the bed, mostly turned to wood. He tells Emma she can succeed without him just before completely turning to wood. ("A Land Without Magic")