Leslie-Anne Huff

When his experience in the Phoenix stone leads him to do the unthinkable, Damon finds himself without a care in the world, spiraling out of control and under the influence of a dangerous and reckless Julian (recurring guest star Toddd Lasance). Refusing to give up on his brother, Stefan attempts to reason with Damon, only to uncover the devastating reason for his descent. Elsewhere, Caroline begins having some dangerous side effects as a result of her supernatural pregnancy and is forced to turn to Valerie (recurring guest star Elizabeth Blackmore) for help. Meanwhile, Bonnie, Nora (recurring guest star Scarlett Byrne) and Mary Louise (recurring guest star Terressa Liane) attempt to track down a ruthless vampire hunter named Rayna (recurring guest star Leslie-Anne Huff) after they suspect that she has reemerged.

In order to lure a vengeful vampire hunter named Rayna Cruz (recurring guest star LESLIE-ANNE HUFF) away from his friends in Mystic Falls, Stefan heads to New Orleans, where Valerie (recurring guest star ELIZABETH BLACKMORE) has learned of a safe house that can protect him. Once there, he comes face to face with Klaus Mikaelson (guest star/former series star JOSEPH MORGAN – The Originals), who soon becomes suspicious of his old friend's unexpected arrival in his city. Meanwhile, Enzo, who is working on behalf of a mysterious organization called The Armory, approaches Damon and Bonnie with a plan that could protect Stefan from Rayna. Finally, after learning that Alaric has decided to leave for Dallas with the twins immediately, Caroline offers to accompany them on the trip and finds herself contemplating her own future in Mystic Falls.

When complications from her supernatural pregnancy leave Caroline's life hanging in the balance, Stefan and Valerie (recurring guest star ELIZABETH BLACKMORE) take extreme measures to try and save her and the babies. Meanwhile, after uncovering a dark secret about Damon, Enzo uses the information to force Damon into helping him track down Rayna Cruz (recurring guest star LESLIE-ANNE HUFF), a ruthless vampire hunter who is on the loose. However, when Damon's actions inadvertently put everyone he loves in Rayna's path, he is forced to make things right before it's too late.

While Stefan and Valerie (recurring guest star ELIZABETH BLACKMORE) search for a magical herb that can keep him hidden from Rayna (recurring guest star LESLIE-ANNE HUFF), Damon comes up with his own plan to take her down for good. However, while at The Armory, Bonnie makes a shocking discovery about Rayna that brings Damon's plan to a screeching halt. Elsewhere, a conversation with Caroline leaves Stefan questioning their future together, while Matt decides it may be time to truly take a stand against the vampires of Mystic Falls. Damon's desire to take himself out of the game ramps up as he races to complete unfinished business with Stefan and Bonnie.

In an attempt to make things right with his brother, Damon offers to have Stefan's scar magically transferred to him, only to discover that doing so may come with some unexpected consequences. With time running out and Rayna (recurring guest star LESLIE-ANNE HUFF) closing in on Stefan, Valerie (recurring guest star ELIZABETH BLACKMORE) desperately attempts to reason with Damon before it's too late. Elsewhere, after being framed for breaking Rayna out of the Armory, Enzo attempts to clear his name, but not before a violent run-in with Nora (recurring guest star SCARLETT BYRNE) forces him to make an upsetting discovery.