Obann

 is a mysterious fiend with ties to Yasha's forgotten past. As an NPC, is played by Matthew Mercer.

Appearance
is a red-skinned fiend with horns, yellow eyes, a tail, and leathery wings. In his appearance at the Overcrow Apothecary in Rosohna, he was disguised as a drow wearing a long tattered black cloak pulled around a set of gray leather armor, his features obscured with a hood and a facewrap of blue cloth. After his death at Yasha's hands, his punished form becomes a grotesque mass of tentacles.

Personality
seems to regard the Mighty Nein with amusement, despite the threat they pose, as evident in his voice before charming Nott, and his reactions to Jester's attempted deception and singing. He seemingly has no qualms with leaving his associates behind to die.

Background
The Cobalt Soul in Zadash holds a single tome mentioning 'Obann'. It says that he once served Graz'zt, the Dark Prince of the Argent Palace within the Abyssal domain of Azzatar, as his Master of Wills. He was shamed and destroyed after a terrible failure to his lord.

Obann was unaware that he was serving the Chained Oblivion. He truly believed in the Angel of Irons, and only realized the truth as Tharizdun killed and reformed him.

He was again punished by the Chained Oblivion for failing to break the first shackle beneath the Chantry of the Dawn. After Yasha killed him, his body was turned into a mindless monster.

appeared in Yasha's vision on the Ball-Eater during a storm. She sees a muddied field of burning huts, corpses lying at her feet, her blade bloodied. A figure turns to her, eyes aglow with yellow, their deep red skin and hooked horns peeking from beneath their folded wings. Their smile curls open. "Your anger is beautiful to behold, Orphan Maker."

During Yasha's dream-vision in the Braan, she sees dozens and dozens of bodies tumbled before her, and turns to see a familiar male figure, curved horns back from the front, his wings folded over his shoulders, with a sly grin and yellow eyes. He just looks and walks away, shaking his head. The figure is familiar to her, but she doesn't know why or where, and causes something in her heart to freeze and fear to well in her throat.

entered the Overcrow Apothecary along with a hobgoblin guard and was given a crest by a Dragonborn messenger. As the fight broke out, he charmed Nott and used Dimension Door to escape. As he fled, Jester cast Sending using a fake voice, telling "Eyes are on you. You've left the rendezvous. What happened to the mission?" He replied, "I know you. But I appreciate your attempt at deception. If you are intent on following, come north. Bring her."

Jester managed to scry on walking along the base of the Penumbra Range Mountains, searching for something using the crest.

After their arrival in Bazzoxan, Jester casts sending on again, saying, "The Orphanmaker has arrived. Where can we find you?" and filling out the rest of the message with vocalizing. says "Expedient and trustworthy. I am impressed. And a performer. Come five, six miles west of the village. Look for the hidden entrance. I'm waiting."

Before their long rest by the bridge, Jester sends, "This place is really scary. We have her. How far is it? What is this place? Did you know there were gold hearts? Okay, anyway, bye." replies, "Oh, yes. I've made my way as well. I'm glad you've kept up. Hope to see you soon. Just be careful. Wouldn't want you spoiled."

Obann confronts the Mighty Nein in an underground chamber in the Penumbra Mountains, where he shows his true form and reveals some of what he knows about Yasha. He tells the Mighty Nein Yasha was traveling with him following the commands of "The Angel of Irons". He has come to this temple to release one of the children of the Angel of Irons. He begins reading from a stone tablet so the Mighty Nein attack. After a huge fight, he is eventually killed by Fjord and with his dying breath tells Yasha to avenge him.

While Scrying, Jester sees Yasha perform a ritual that apparently brings Obann back to life. He touches her shoulder and says, "Very good. Thank you for your patience. Now this has been one fine reunion. Let's go see if we can find the others."

Jester scries on Yasha once more and sees Yasha, along with and The Laughing Hand attacking the Cobalt Archive in Zadash, searching for information about a creature named Jourrael.

The Mighty Nein's research in Zadash inform them that Jourrael was an assassin of Lolth whose body was divided up, with the head in Veluthil (now known as the Savalirwood) and the heart in the Lotusden Greenwood. While Scrying, Jester sees Obann, The Laughing Hand and Yasha on the outskirts of the Lotusden Greenwood. Yasha is cutting down trees and Obann seems frustrated and unsure of what to do.

The Mighty Nein pursue Obann into the Lotusden Greenwood. When Jester scries on Yasha, she sees her sitting around a fire next to him. He tries to grab Yasha's chin, and when she refuses a sigil on the back of her neck flares and she stops resisting. They notice he has something skull-shaped in a bag at his waist. Despite the party's efforts, Obann beats them to the Wraithroot tree and recovers a glowing blue stone, escaping with Yasha.

After the party destroys the Permaheart, Allura Vysoren scries on the Laughing Hand and discovers him in poor condition, being berated by Obann for falling apart "near the finish line", an event coming soon.

While scrying on Yasha, Pumat Sol sees her, Obann, Jourrael, and The Laughing Hand entering Rexxentrum. Jester later scries again and sees the group walking through the streets, soaked in the rain.

After the party kills Respa and several other cultists, Obann, Yasha, Jourrael, and The Laughing Hand emerge from the basement. After Yasha is freed from his control, and Obann himself is injured, he uses an ability to charm Nott and tells her to follow him below, then flees. After killing The Laughing Hand, the Mighty Nein follow him to a secret room hidden beneath the temple. They free Nott, and Fjord uses Star Razor's See Invisibility to find an invisible Obann flying above, then uses Faerie Fire to make him visible to the others. Obann tries to charm Fjord to step into a ritual circle, but is thwarted by Caduceus. Eventually Yasha pulls off Obann's wings and stabs him through the chest. They hear the voice of the Chained Oblivion condemning Obann for his failure, and Obann's body transforms into a horrifying monster.

As Obann the Punished, Obann is perhaps even a more difficult opponent than previously, gaining new abilities and legendary actions. The Mighty Nein come into the battle almost fully depleted of spell slots, and many at very low health. At the low point of the ensuing battle, Beau is unconscious with two failed death saves, Jester is unconscious, and Caduceus is swallowed. However, the now-free Caedogeist comes to their aid, also attacking the creature, and striking the blow that kills it, presumably ending the life of Obann permanently.

Tharizdun
It was revealed in that Obann had made a deal with Tharizdun in order to make himself stronger. Obann didn't know that the Chained Oblivion was actually the one behind the Angel of Irons Cult until moments before his gruesome punishment.

Yasha Nydoorin
has a connection to Yasha's past, recognizing her on sight and addressing her as "Orphan Maker", which is her tribal name and not widely known. Yasha does not recognize him in return. Later, he is revealed to have been the fiend haunting Yasha's dreams, and the one who recruited her into the followers of the Angel of Irons during the time in her life she had forgotten. In his dying moments, Obann tells Yasha to "avenge him" and she falls under some form of magical influence which dictate her actions and return her forgotten memories. She becomes trapped within her mind, aware of what she is doing, but unable to control her body. After Yasha regains control of herself, she tears off his wings and strikes a final killing blow to him.

Abilities
is a spellcaster.

1st-level

 * Shield

4th-level

 * Dimension Door

5th-level

 * Dominate Person

7th-Level

 * Plane Shift

Notable Items
Abyssal Longsword

Abilities as Obann the Punished

 * Huge monstrosity
 * Legendary Actions: three per turn
 * Inky Whip: Makes one Inky Whip attack
 * Shadow Slip: teleportation
 * Spill Darkness: (costs 2 actions) 20 foot radius around caster engulfed in magical darkness
 * Storm of Biting Shadow: 30 foot radius for necrotic damage and weakened condition, individually targeted, rolls to recover ability
 * Multiattack: on its turn, can make three tentacle attacks and a bite attack
 * Inky Whip: tentacle attack, does necrotic damage and pulls target 10 feet to a space adjacent to attacker
 * Jagged Bite: does piercing damage, and on failed strength saving throw, swallows target making them blind and restrained
 * Damage Immunities: poison
 * Senses: blindsight

Quotations

 * "Your anger is beautiful to behold, Orphan Maker."
 * Matt: (describing Obann's revealing his true form in the temple in the Penumbra Range) "You watch as his form begins to slightly shift. The drow dropping away- leaving behind red skin, yellow eyes, horns that curl up across the head, and a pair of red leathery wings that lie folded across the back."
 * "Angel of Irons... why have you abandoned me? I did everything you asked..."