THE DEVIL FROM CHRISTMAS PAST — Faced with the fallout from his interaction with Cade, Stefan is determined to have one thing go right – Christmas Eve with Caroline. However, when Damon and Sybil crash their Christmas Eve dinner, which had been joined by Alaric, Matt and Peter, things quickly take a dark and twisted turn. Meanwhile, in a series of flashbacks to Stefan's past, Cade's tempt to entice him with his mysterious agenda leaves Stefan faced with an unimaginable decision. Bonnie and Enzo also appear.
- Antagonists: Stefan (flashback), Damon and Sybil.
- This is the eighth and last mid-season finale of the series. This is also the first mid-season finale to be on the seventh episode.
- For the first time, Damon and Stefan have their humanity off at the same time.
- Cade tells Stefan that until he meet Elena she was headed on the right path but by Stefan meeting her made Elena into something dark. This indicates that Elena could end up in Hell. Cade tells Stefan that souls like Elena's who would just squeak by into Heavan are the ones he wants Stefan to go for.
- Cade accepts Stefan's deal that he and Damon will serve him for only 1 year and will not go to Hell.
- The Ripper of Monterey event in 1917 is revealed to happened at Christmas time and that Seline was a witness to it.
- Cade is the third person, after Klaus and Caroline, to make Stefan become the Ripper.
- Damon rips out Sybil's heart after seeing her wearing Elena's old vervain necklace, seeming to indicate he remembers Elena as the woman he loves.
- When Seline asks Tammy to sing her "something nice and easy" tammy sings "O Holy Night" - the song that was playing in the first Christmas episode - O Come, All Ye Faithful.
- The song was playing when Klaus kills his hybrids.
- Inhabitants of Monterey - Blood loss; killed by Stefan (flashback)
- Stefan Salvatore - Stabbed with wooden ornament; killed by Damon (temporarily)
- Sybil - Heart extraction; killed by Damon (temporarily)
- Monterey (flashback)
- Mystic Falls, Virginia
- Grove Hill, Virginia
- This is the eighth mid-season finale to feature Stefan and Damon; the seventh to feature Bonnie, Caroline and Matt; the fifth to feature Alaric; the third to feature Enzo; the first to feature Cade, Sybil, Seline and Peter.
- This is the second mid-season finale not to feature Elena.
- This is the series' fourth and last Christmas episode.
- This is the second episode in which two vampires have their humanity off at the same time.
- This is the final episode to air in 2016.
Behind the Scenes
- "The Next Time I Hurt Somebody, It Could Be You" is a line from Stefan from season one's Blood Brothers.
- With its thirty-six letters (ten words), this episode has the second longest title in the series.
- Hashtag during the airing is #DecktheHells