In Day One of Twenty-Two Thousand, Give or Take, Lillian is shown to be helping her fellow Heretic members adjust to the modern world. Lily visits Enzo in New York and asks about a stone. When the Heretics cause chaos at the deputy graduation, Lily arrives and is angered for what both parties have done. After the events at the deputy graduation, Stefan and Lily broker a deal, which is any person who comes into Mystic Falls are the Heretics.When Malcolm is killed, Valerie, Nora, Mary Louise and Beau don't want to tell her, but she sees his corpse and starts to cry. She asks who is responsible angrily and she lets them retaliate once again, which is by taking Caroline.

In Never Let Me Go, Lily confronts Stefan with Beau and tells him about Malcolm's death. When she realizes he doesn't know anything about it, she tells him that she's not here to blame him, but so he would understand what they had to do. Lily is then met at the door by Damon and he asks for a switch with him and Caroline. She tells him that Malcolm was a powerful Heretic and has a hard time believing he acted alone, and Damon says he's just awesome. She tells him she and the others don't think he is, and when he tries to stop her from closing the door on him again, he sees that he can't walk into his house. She coldly tells him it's because it isn't his house and she tells him she has go bury her son. She walks into the room where Enzo and is wondering why he isn't watching her. He tells her she temporarily escaped and now Nora and Mary Louise have taken over. She pauses for a moment and tells him that she and the others are leaving for the cemetery, and she needs him to stay at the house. Lily and the others at the Salvatore Crypt and she tells them to put Elena's coffin in the river. When Damon gets angry that Elena is gone, Lily remarks that he always had the worst tantrums. She mocks him saying that's the beauty of cloaking spells, she could be next to him or a million miles away and only she would know where she is. She calmly asks if he remembers what he did to her grandmother's vase and how she took is toy soldiers away, he tells her Elena isn't a toy soldier, but she remarks that Malcolm wasn't a vase. She tells him that Malcolm was a vital part of the family and the other Heretics are seen behind her. She says that Malcolm was her sounding board, her confidante and her eldest son. Damon then makes a deal with her to get out of Mystic Falls. She and the others arrive back at the house and asks Enzo if he wanted her to talk to the girls about letting Caroline stay with him. He tells her Caroline made her own bed and he tells her that he chose her. After Enzo brushes a lock of her hair and tells her which bedroom he is taking, Lily looks visibly affected by Enzo's confession.

In Age of Innocence, Lily is working on her driving and is confronted by Stefan. He tells her that she needs to tell her spoiled brats to stop torturing Caroline and she says she will if Damon would stop killing said spoiled brats. He puts up the ruse that he and Damon have concocted, and she reveals to Stefan that she sent Valerie to him so she would know that he and Damon were okay. She also reveals she had a vampire boyfriend named Julian and that he was a man you weren't supposed to fall for, but she did anyways. While they talk, Stefan teaches her how to drive and he tells her that he didn't forget her, but that they he found distractions. He later tells her that Valerie had sent him a telegram telling him that she would be coming back for him, to which Lily is shocked to hear. Lily then goes into the room where Caroline is and asks if Valerie is there. She tells her no and Lily says she heard about Caroline's mother dying, to which she asks her how to heal after such a loss. Caroline then tells her that love is different than any other kind of love and she says Stefan wrote about her a lot in his journal, handing it to her. She then yells to Nora to remove the barrier spell and that it is a reward for Stefan's honesty. When Caroline leaves, Lily continues to read Stefan's journal. She gets a call from Damon and he reveals to her that he has Damon and that he knew about Gettysburg of 1863. When Damon tells her to give him Elena back and he'll give Oscar back to her, which leaves Lily with a murderous look on her face after the call.

In I Carry Your Heart With Me, she is talking to Damon on the phone in the car and it is seen that she has Elena's coffin in the back. She tells him that even though she gives Elena back, she'll still be in a box and that he's actually being selfish about it. She tells him if he's harmed in any way, but he interrupts and says that this isn't his first hostage swap. Lily walks into the house alone and tells Enzo that she needs to speak to Valerie privately. She reveals that she knows and Stefan and Valerie's tryst back in 1863. She tells Valerie if she has anything to tell her now is the time and Valerie says she has nothing to hide. When changes the subject about looking for Oscar, Lily tells her it won't be necessary. Lily is sitting near the fireplace and she is asked by Enzo who Julian is. Before she answers about Julian being the love of her life, Damon sends her a selfie of him and Oscar, which immediately cheers her up. She quickly gets up and leaves to meet up with Damon. Lily is then horrified by what Oscar is doing with tourists and tells him enough. She asks what has gotten into him and he growls at her. Threatened by Oscar's glare, she trips and falls backward on the ground. Damon then appears and snaps his neck before he could harm her, which shocks her. He then asks where Elena is, which makes her frown. After Damon sets the tour bus on fire, Lily tells him she told Beau to take the cloaking spell off Elena's coffin and that it can be found in the ruins of the old Salvatore mansion. He tells her he's moving back to Mystic Falls and she says she and her family will take into consideration. He tells her that the people don't deserve to die by her children and she then gives him some advice. She tells him he's just putting himself and Elena's body in jeopardy. She gives him a statement on how there would no skin off her nose if he returns to Mystic Falls and he asks for one more favor.

In Live Through This, Lily comes into the room to see Oscar drinking many of the blood bags. She smiles at Enzo and tells him it was kind of him to sit with Oscar all night. She tells him that she's expecting Julian to be home if everything goes as planned. She hopes he can be happy for her and that there's no reason for them that they shouldn't get along. She asks Enzo if he could keep an eye on Oscar while she, Nora and Mary Louise go out, and he feigns being polite and happy to help. She also asks him if he hears from Valerie, to tell her to come home as there's no reason to sulk. Lily walks into the warehouse where Mary Louise and Nora has found Valerie trying to burn Julian's body. She tells Mary Louise and Nora that she'll meet with them in the car and confronts Valerie. She tells Lily he's a monster and she slaps Valerie across the face. She tells Damon and Stefan that Julian is the love of her life, and when the two refuse to stop Lily and Beau, Valerie reveals to Damon that Lily was the one who gave Kai the idea about the sleeping spell. He becomes furious, puts Lily in a choke hold and declares he'll kill her instead. Beau then magically flings Damon into one of the shelves of coffins and makes the coffins explode into a shower of wooden shards. Lily and Enzo are talking in Stefan's old bedroom, and he tells her Oscar died two nights ago. She reveals to him that a soul in the Phoenix Stone has to be reunited with its proper body. She asks him for the stone and she asks if he's wanting her to choose between him and Julian, to which he says yes. She caresses Enzo's face with tears in her eyes, and she asks him to understand, and Enzo leaves the room devastated. Lily is then seen standing around a table where Mary Louise, Nora and Beau complete the spell to bring Julian back into his body. Lily rushes over to him when he awakens and asks if it is him, which he confirms it is. They then embrace, laugh happily and then kiss passionately.

In Best Served Cold, Lily arrives into the room where Beau and Julian are fencing, and tells them to take it outside. She tells them they have enemies in Mystic Falls and when he thinks it's Valerie, she tells him it's her sons. Julian is shocked that her sons are alive and she nods in confirmation that he has a lot of catching up to do. She sends them an invitation that requires their presence and they realize Julian has been resurrected. Lily opens the door to see Stefan and she tells them she had Lucy sign the house over to them. She tells him that she wants to him that her family is civilized and nobody is in danger. She then greets Enzo and Bonnie at the door, and she hopes she and Bonnie could start fresh. Bonnie tells her that Lily is the reason she won't be able to see Elena again. She then stops the jazz singer and asks if in time that everyone can accept each other, restore the town and live in a state of peace with the residents. Lily then sees Bonnie fixing Enzo's tie and is visibly a little jealous. After Stefan attempts to kill Julian, Lily walks in wondering what is going on. She asks him what she has done wrong and before he answers, Damon walks in. Julian has Damon and Stefan sit down, and then tells them about his personal hell in the Phoenix Stone. He reveals to them how he had to relive the day over about killing Lily. When Julian throws a knife at them, Lily yells at him and before he does harm to Damon anymore, she pulls him away. Before he strikes Lily, he realizes what he has done and tells her sons to get out. She asks about what happened in his blind rage and tells him she was trying to end the feud, not start a new one. She tells him she has no desire to see her children and if he has a problem with that, then they have a problem. When he tells her that he thinks that hell he has gone through isn't gone yet, she softens and tells him that they'll fix it, but he needs to promise her the events that happened wouldn't occur again. When he tells her he needs to feel safe as he knows that her sons will strike again, Lily tells him that what he wants will take the cooperation of the entire family.

In Mommie Dearest, Lily arrives at the Lockwood Mansion with cranberries for Thanksgiving. Stefan tells her he invited her over so they can start over. He tells her he wants to convince her of all the reasons they need to get rid of Julian. He tells her how he got Valerie pregnant and how Julian killed the child. She says that Valerie had lied for all those years and Stefan fakes that he shouldn't have believed Valerie either. He pours them glasses of bourbon and when she drinks it all, her mouth begins to sizzle and burn, to which Stefan reveals to her it's concentrated vervain. She then collapses on the floor and the boys tie her up in a chair. He tells her that she has fallen back into a pattern with terrible men, from their father to Julian, and they're going to convince her to come to light about him. Stefan then brings up a memory about what happened back on Thanksgiving in 1851 and how Damon got blamed for taking some money. Lily tells them that she tried everything for them, but before she could finish, she cuts a cut on her neck and tells them that she and Julian's life are linked, so if he dies, so does she. She reveals to Stefan that she took the money since Giuseppe never let her have anything or access to funds. She then tells him that she was going to take him and Damon away from their father, but even drunk, Giuseppe was a step ahead. She tells her that she wasn't blind to what Giuseppe was doing and that she was doing it all for her, Damon and Stefan. Her knees then buckle and more wounds begin to be inflicted on her because of linkage to Julian. She and Stefan then arrive at the cemetery to stop Julian from killing Damon. When Julian tells her that drove a sword into his chest to kill him, Lily tells Julian to take her home while still looking at Damon. She asks what Julian was doing with Lorenzo in the woods and he tells her that he doesn't resist a sword fight, but Lily says her life was tied to his and they both could've been easily killed. When she asks if he knew about Valerie being pregnant, he plays dumb and says he didn't. He notices the conversation isn't going anywhere and asks if she would forgive him for acting as though the day's events were nothing. She answers, unsmiling, "Of course", and when he hugs her, the look on her face is shown that she realizes what kind of man Julian really is. Lily then goes to the Lockwood Mansion and asks Damon if she can come in. She tells them that they were right about Julian and that she's not going to let him hurt them any longer, as she has a plan.

In Hold Me, Thrill Me, Kiss Me, Kill Me, after entering the kitchen and asking what the fuss was about, it is revealed that is is Nora and Mary Louise's Anniversary today. Lily tries to hide the fact that she has forgotten, aided by Julian who tells the girls that Lily has planned something special. While searching through the various shelves of books, Enzo walks in the room he confesses he loves her. When she tells him that she can't abandon her sons and their plan to kill Julian, he kisses her and he gives her good luck as she's going to need it. When she walks into the party room, she reminds them that they only feed on trespassers and she then backtracks, telling them that they can make an exception as it's their day. While the others feed on the party guests, Lily texts Stefan the location of where the party is. While taking Nora aside in the backyard, she gives her the anniversary gift of the book she read in the Prison World. Julian comes behind her and he asks her to dance with him. She tells him she doesn't know how to dance the music playing, an old song comes on instead and Julian asks if she recognizes the vocals. She remembers that it's Beau singing before he lost his voice, and Julian then tells her to feed on one of the guests. He then mentions the friction that's happening because she's holding onto the fact that she thinks Stefan and Damon will join their family. He shows her a guest with a bloody bite and she begins to vamp out and feed on her. Damon then arrives and looks at her in disgust, which causes Lily to quickly pull away and licks the blood off her lips. She then chases after Damon and tells him she had to convince them that she's on their side. She tells him that the plan must go forward as she doesn't want to be around Julian anymore. When Damon goes to far, she slaps him across the face and says she's his mother, and she asks why he's cavalier about her life. He tells her she's dead to him and that if he had to do it all over again, he would leave her in the Prison World so that he wouldn't have to see her face. After he leaves, she looks visibly hurt and worried. She and Valerie then go to talk to Mary Louise, Nora and Beau to get them to be on their side. Lily confirms Julian killed her grandchild and she says after what Valerie told her, she says that all the lights came on and that she decided that Julian needs to go. After Beau and Nora see the truth, they agree to help and Lily texts them that the Heretics are now on their side. While in the shed, she is visibly nervous and asks Beau to come over to her, as she is preparing for what's to come. While Stefan and Damon do their thing with Julian, Lily feels his pain and starts to bleed. After Julian is tied, she talks to Stefan and he reveals that Caroline is pregnant. She gives him some advice and he turns give her some about Damon. She smiles when she realizes she has reconnected with Stefan and when he tells her she needs to give Damon time to forgive her. Lily then walks into the room where Damon and Valerie are tied up, and is horrified to know what is going on. He tells her she has to choose who lives and who dies, and Lily is very conflicted. She then turns and faces Julian, and she then tells him that she can choose both. She then lifts the stake in the air and drives it into her own heart. Julian then reveals to her that he had them already unlinked and she starts to cry. Lily is lying down in the lounge and Nora says she can't get the splinters out. Stefan then tells Nora that it is time to say goodbye and Beau, Nora, Valerie and Stefan each say their goodbyes. Valerie tells Damon that Lily only has moments and he should make the most of them. Lily tells him that she's truly sorry and when he looks as though he's about to forgive her, he tells her that she made her bed and to have a nice nap. Lily then desiccates and dies, leaving a hurt and disappointed look in her face, with a single tear falling down.

In Cold as Ice, Damon, Stefan, Nora and Valerie bury Lily near the family plot. They each say their goodbyes, except for Damon who tells her she was a terrible mother alive and in death. When he leaves, Stefan tells her he'll make things right.

In Hell Is Other People, Lily appears as a hallucination to Damon in his personal hell. In the last hallucination he has, she is stuck underneath a wheel of cannon and asks why he is delighting in her pain. After many confessions of why he hates her, he finally tells her the truth that he hates that she never came back and after three times of losing her, he kept failing in telling her everything he wanted to say, and yet those three times he ruined it. She tells him that there's still time to say what he wants to say and he tells he's sorry and if she could give him the chance to make it right, to which he realizes she's dead.