In the Land of Oz, Mulan and Ruby meet up with Dorothy while dealing with Zelena after she returns from Storybrooke, but a series of events bring Ruby to the Underworld. Meanwhile, David and Snow must find a way to return to Storybrooke, and Belle comes up with a solution to save her and Gold's unborn child.
Red walks around the red-tinted forest.
In The Character's Past
In the Land of Oz, Red and Mulan are running in the woods when Red's senses start to pick up a smell, followed by a growl, and they come across Toto. They then encounters Dorothy, who believed that Toto sniffed out a witch, meaning Red, who had to explain to Dorothy that she is a lycan. After the introduction, Dorothy notices Toto whining and races off, as Red tells Dorothy he went the other way. They noticed a tornado has brought back Zelena, who wants her slippers. Dorothy refused to hand it over until Zelena shows her that she has Toto, so she gives her 24 hours to hand it over or Toto is killed. Later that night, Mulan, Ruby, and Dorothy start brewing the cauldron, when Dorothy discovers they need poppy seeds, so Ruby comes along to help her. During the walk, Dorothy tells Ruby about Aunt Em, who had passed away. As Dorothy hands Ruby a poppy, Ruby tells Dorothy she killed her boyfriend, Peter. The conversation is interrupted by the winged monkeys, prompting Ruby to transform into a wolf, and Dorothy gets her red cloak and she takes off on her own to look for Toto. Moments later, Mulan and Ruby discuss about what Dorothy said to Ruby, but when Ruby goes to Dorothy's house she finds a plain of cloth of Aunt Em's. At the palace, Zelena caged Toto as bait to trap Dorothy. Zelena then pricked Dorothy on her back and is placed under the sleeping curse.
In the Underworld
At Granny's, Ruby is lying down in bed and wondering why she’s in the Underworld. Emma then finds a piece of plaid clothing and shows it to the others, as Ruby wakes up to tell them she was tracking Zelena because Dorothy went missing. She says she destroyed another life because she’s a wolf but Snow promises to help them. Emma says they need to go talk to Zelena, who by the way, is suddenly informed by Hades about Ruby's entry into the Underworld and is now is afraid that Ruby will reveal more of her past deeds and that Regina will take her baby. Zelena decides that she must leave the Underworld, despite a plea from Hades to stay. David is with Hook and Henry walk to phonebooth. At the phonebooth, Cruella orders her men to destroy it at the expense of the disgruntled residents as David attempts to make another call. Henry asks if this is because he won’t bring her back to life, but Hades ordered Cruella to remove it to kill the hope they’re encouraging. Cruella offers David a deal that he turns down, prompting Cruella to order her henchman Claude to rip out the phone, leading David and Hook to believe that Hades is trying to keep the outsiders from contacting the overworld.
As the group confronts Zelena about Dorothy, she tells them that she put Dorothy under a sleeping spell that can only be broken by true love’s kiss, but there is no one who actually loved Dorothy. Zelena however turn over the magic slippers, which doubles as a portal out of the Underworld, and wishes Dorothy the best. Ruby realized that the only relative Dorothy loved, Aunt Em, is in the Underworld and they find her working at a diner that she operates. Emma attempts to have Aunt Em blow her kiss into a bottle, but thanks to Hades she turns into slime and warns the Underworld residents that if they help the outsiders they'll be met with the same demise. Hades then squeezes Aunt Em's soul into a jar. Back at the loft, Hook talks to David about how he and Snow will go home to see Neal knowing that being without frustrating. At the graveyard David trades his wife's name on her tombstone for his so Snow could go home to Storybrooke with the help of Hook. Ruby then uses the silver slippers three times to take her and Snow back to Oz. Henry's illustrated visions revealed to David that Snow made it back to Storybooke.
In between the events, Belle visits Zelena to ask for help in preventing Hades from accelerating her pregnancy the same way Emma did with Zelena. Later on, Belle shows Gold a spindle that will put her under a sleeping curse in order to allow Gold to break the contract and prove to Belle that he can change. As she pricks her fingers before going under, Belle tells Gold about her father's true love kiss, which can be used to save her if Gold fails. After Belle leaves, Zelena arrives at Hades' lair, where he pours Aunt Em's soul into Acheron, which he did as a symbol of his love for her. Hades and Zelena then drink and make a toast after she agree to his offer, although Zelena did not tell him about Ruby and Snow escaping the Underworld to save Dorothy after she gave the slippers to them, as he assumed the curse was still in effect.
In the Land of Oz
Ruby and Snow end up in the Land of Oz. Mulan is with the Munchkins and Toto when Dorothy was under the sleeping curse by Zelena. Ruby tells Mulan that she found Dorothy on the bed. Snow encourages Ruby to kiss Dorothy and they embrace. Later on, Ruby takes Snow back home to Storybrooke by using Dorothy's silver slippers.
- This episode marks the first LGBT relationship in the show's history - between Ruby and Dorothy.
- The title is a reference to the Silver Slippers and the character Ruby, as well as the Ruby Slippers from the 1939 movie.
- This episode marks the first appearance of Aunt Em in the series.
- This episode marks the final appearance of Ruby, Mulan and Dorothy Gale.