Emma, Regina, Mary Margaret, David, Robin, Henry and Gold arrive in the Underworld, on a mission to rescue Hook, only to discover that their search will be more difficult than they had anticipated. The inhabitants of the Underworld — all souls with unfinished business and many with quite personal vendettas — hound our heroes at every turn. Meanwhile, in an Enchanted Forest flashback, a familiar face from the Evil Queen’s past returns to present Regina with the perfect birthday gift.

The heroes join forces with an old friend of Snow's to defeat an obstacle standing in the way of finding Hook. Meanwhile, Hook encounters challenges of his own.

Hook's captivity takes a dark turn when Hades threatens to condemn him to the River of Lost Souls after Hook refuses to choose which three of his friends will have to remain in the Underworld. Meanwhile, Gold is suddenly eager to help Emma, Snow, David, Regina, Robin and Henry find Hook so he can return home to Belle; but in order to do so, he must find his ex-wife Milah in the Underworld and ask for her help. In Fairy Tale Land flashbacks, Rumple and Milah face a life-or-death crisis concerning their son, Baelfire, that forces Rumple to make a deal that will haunt him.

In Underbrooke, Hook questions whether he is worthy of forgiveness after meeting his brother Liam. In the past, Liam makes a deal of his own to save himself and his brother... at the cost of a ship's worth of men. Meanwhile, Henry meets the Apprentice and learns of his true power.

Emma, Snow, David, Regina, Robin, Henry and Hook continue to search for a way to free everyone from the Underworld. At the mercy of Hades, Gold creates a portal to Storybrooke, which transports Belle, Zelena and Baby Hood to the Underworld. While Zelena and Regina get into a sibling squabble, Belle is reunited with Rumple only to learn some tremendously shocking news that will change her life forever. Meanwhile, Snow and David hopelessly attempt to send a message from the Underworld to their son, Neal. In flashbacks, Hades learns about Zelena’s very special spell and pays her a visit in Oz with the intention of striking an alliance, but finds himself with more than just a partner in crime.

Belle turns to Rumplestiltskin with hope of finding a way to protect their child from Hades. However, they disagree over whether to use dark magic, as Belle forbids Rumplestiltskin from using his powers for evil. Meanwhile, Hades secretly meets with Gaston in the Underworld and encourages him to seek revenge on Rumplestiltskin. As the heroes try to find a way to defeat Hades, Emma has a terrifying nightmare that she realizes is beginning to come true. And in flashbacks, Belle and Gaston meet for the first time, but their blossoming romance comes to a halt on the eve of the Ogre wars.

In flashbacks, Ruby and Mulan find themselves in Oz, where they meet Dorothy. After the three witness Zelena’s return to Oz, they look for a way to defeat her once and for all. However, Dorothy mysteriously disappears, and Ruby’s search for her new friend lands her in the Underworld. Reunited with the heroes, Ruby teams up with Emma, Regina and Snow to continue looking for Dorothy. Meanwhile, Snow and David struggle with not being able to be with their son, Neal, and devise a plan so that one of them can escape the Underworld.

Now that Hades and Zelena are reunited, Hades tells Zelena that he wants a future with her outside of the Underworld. All she needs to do is heal his heart with True Love’s Kiss so they can leave the Underworld and trap the heroes there for eternity. When Regina overhears of this plan, she enlists Cora’s help to find a way to separate Zelena from Hades. However, Cora reveals a family secret that could change Regina and Zelena’s lives forever. Meanwhile, David finally meets James, only to realize that his twin is determined to seek revenge on him for stealing the life he could have had.

Hades turns to the heroes to ask for help with getting Zelena back from Rumplestiltskin and Peter Pan. In return, he offers to take all their names off their tombstones. However, when Hook is still unable to leave, he and Emma must journey into the depths of the Underworld. Meanwhile, Cruella De Vil is determined to keep the heroes trapped in the Underworld. In flashbacks, Emma searches for answers about her family and makes an unexpected friendship.

Emma, David, Regina, Robin and Henry are finally back home in Storybrooke and reunited with Snow, but, unfortunately, they still have to contend with Hades, who continues to deceive Zelena as he lays out his plan to use the all-powerful Olympian Crystal to take over the town. The heroes desperately search for a way to defeat Hades while Hook does the same in the Underworld, looking for those missing storybook pages. Regina and Robin take a more direct approach, which culminates in an epic showdown that will leave our heroes forever changed.