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")
During October 2011, August is living a relaxed life in Phuket, but awakens one morning 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 is unable to see the wooden state of August's leg. In his desperation, August stabs himself in the leg with a knife to prove it, but instead frightens the doctor, who calls security. After fleeing the office and 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, she walks out from the office to notify him that is it now his turn with the healer. Once alone with the Dragon, August purposely shows him his right non-wooden leg to see if the man is a true healer or a fraud. The Dragon is aware it is actually his left leg which is wooden, and also demonstrates knowledge about August's true identity as Pinocchio. For a cure, the Dragon asks for payment with an item of great and precious value to August; something close to his heart. August gives up a necklace with a small whale-shaped ornament, which his father once used to animate him as a puppet. For the second half of the payment, the Dragon requires ten-thousand U.S. dollars, though August cannot afford it. While mulling over this, August meets Tamara in a street bar and joins her for a drink. As she pays for his beer, he is stunned to see her handling a very large envelope of cash. They converse about their reasons for visiting the Dragon; with hers being a rare form of cancer. Tamara excuses herself to take a phone call and while she is away, August takes her envelope of money and delivers it to the Dragon. Before giving him the bottle, the Dragon warns that the physical pain of his affliction is just a symptom and only he can truly cure himself. Outside, August is apprehended by an angry Tamara as he is trying to open the bottle. He runs from her, but a searing pain from his leg causes him to collapse on the street and drop the bottle. Tamara snatches it away, and bitterly remarks that he deserves whatever condition he has. A few days later, he returns to the clinic to ask the Dragon to cure him again, but is puzzled to find the man dead. Finally, August decides to return to Emma's life and convince her to believe in the curse so she can break it. He has hopes that by doing so, his wooden state can be reversed. 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")
Some time later, August rides into Storybrooke on his motorcycle, where he meets Sheriff Emma Swan and Henry Mills 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, due to 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 Blanchard's arrest over Kathyrn'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")
In a deleted scene of the episode, August is seen sitting at Emma's table. He says he would like to ask her out again but knows it is not the best time for her because she was the lead investigator of her roommate's case and Emma agrees with him. He still offers to buy her a drink and Ruby goes to get it for her. He notices that she cannot stop looking at Regina Mills and asks what she plans on doing. Emma wants to give her a piece of her mind but it has not been working out lately. August gives her the advice to try a new approach. She agrees, but the problem is she is the "go over there and give her a piece of my mind" type. August replies that while he loves that about Emma, there are other ways to get what you want. Then he tells her about an advice he got from a toreador he met in Pamplona, "Don't let them see you coming." August gets up and leaves the money to pay for Emma's drink. ("Heart of Darkness")
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.
Emma and August put the chipped shovel piece onto a shovel in Regina's garage and it fits perfectly. Emma tries to confront Regina about it the next day 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, Emma implies that 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, August is seen sleeping in his room at Granny's inn. He seems to be in pain when his left leg appears to lock up on him, and he tumbles off the bed and onto the floor. August painfully drags himself over to the desk and calls someone, stating that "it" is taking too long and they need to accelerate the plan. He meets up with Henry—the person he was speaking to on the phone previously—outside Mr. Gold's shop. Henry says he does not understand how this is part of Operation Cobra, but August asks that he does as he tells him to. He sends Henry into the shop as a decoy while he pokes around in Mr. Gold's back office. After a brief search, August is confronted by Mr. Gold, who begins to question who August Booth really is. During the party at Mary Margaret's welcome home celebration, August tells Henry that the search was unsuccessful.
After investigating August further, Mr. Gold confronts him under the assumption that August is actually his lost son, Baelfire. Mr. Gold apologizes to August and confesses that he never should have let him go. He tells August he has been looking for him ever since and asks him for forgiveness. After embracing, August asks about the dagger, leading Mr. Gold to tell him that he buried the dagger so Regina would not find out. After unearthing the dagger, August takes it and points it at Mr. Gold, attempting to use an incantation against him. Realizing that August is not his son, Mr. Gold threatens him with the dagger and demands to know who he really is. August confesses that he is from the Enchanted Forest and that he is "sick" and needs magic for a cure. Believing him to be useful, Mr. Gold allows him to live in order to get Emma Swan 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")
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")