Cicero is arguably one of the most polarizing characters in The Elder Scrolls V: Skyrim. To some, he is an annoying, high-pitched jester whose presence disrupts the dark, professional atmosphere of the Dark Brotherhood. To others, he is the only true adherent to the ancient tenets of the guild—a tragic figure whose descent into madness is fueled by absolute loyalty to the Night Mother.

Whether you encounter him on a broken wagon near Whiterun or face him at the end of a bloody trail in the Dawnstar Sanctuary, Cicero’s quests are among the most narrative-rich in the game. Navigating his questline requires a mix of combat prowess, investigation skills, and a final moral judgment that can significantly alter your endgame experience.

The First Encounter: Completing the Delayed Burial Quest

Long before you receive your first contract from Astrid, you might stumble upon Cicero on the roads of Skyrim. This encounter is purely optional but provides essential context for his character and sets the stage for your future relationship.

Finding Cicero on the Road

If you travel north from Whiterun, just past Loreius Farm, you will find an eccentric man in jester’s motley standing next to a broken-down wagon. He is transporting a large, ornate coffin containing the remains of his "mother."

The Choices and Their Consequences

When you speak to Cicero, he asks you to persuade the nearby farmer, Vantus Loreius, to help him fix his wagon wheel. This initiates the quest "Delayed Burial." You have two distinct paths:

  1. Help Cicero: You must speak to Loreius. If your Speech skill is high enough, you can persuade or bribe him to help the jester. Alternatively, you can simply tell Loreius that Cicero is harmless.
    • Reward: Cicero will reward you with a significant amount of leveled gold (up to 750 gold at higher levels).
    • Aftermath: If you return to the farm later, you will find it functioning as usual.
  2. Report Cicero: If you find Cicero suspicious, you can talk to a nearby guard and convince them that the jester is transporting contraband or acting erratically.
    • Outcome: The guard will arrest Cicero. Loreius will thank you for getting rid of the "lunatic."
    • The Grim Reality: In our experience, this path has a dark consequence. If you visit Loreius Farm later in the game, you will find the farmer and his wife brutally murdered. A note or local rumors often imply that the "madman" didn't take kindly to the betrayal.

Note: If you have already joined the Dark Brotherhood and started the quest "Whispers in the Dark," this optional quest becomes unavailable.

Entering the Dark Brotherhood: The Whispers in the Dark Quest

Once you have joined the Dark Brotherhood and completed a few initial contracts, Cicero arrives at the Falkreath Sanctuary with the Night Mother’s coffin. This marks the beginning of the internal conflict within the guild.

In "Whispers in the Dark," Astrid expresses deep suspicion of Cicero. He spends hours locked in a room, talking to someone—or something—inside the coffin. Since no one else is allowed in, Astrid tasks you with hiding inside the coffin to eavesdrop on his conversations.

How to Complete Whispers in the Dark

  1. Enter the Night Mother’s Coffin: Approach the coffin while Cicero is away. You will be prompted to hide inside.
  2. The Dialogue: As you sit in the darkness with the mummified remains, Cicero enters and begins a frantic, one-sided conversation. He laments that the Night Mother remains silent to him, despite his role as the Keeper.
  3. The Turning Point: Suddenly, the Night Mother speaks—not to Cicero, but to you. She names you the "Listener" and gives you a specific phrase: "Silence, my brother."
  4. Confrontation: When you emerge, Cicero is initially enraged that you desecrated the coffin, but once you repeat the words of the Night Mother, he breaks down in religious ecstasy, recognizing your divine appointment.

This quest is pivotal because it establishes the rift between Astrid’s pragmatic, "modern" Brotherhood and Cicero’s traditional, religious devotion.

The Core for Madness: A Step-by-Step Walkthrough

The tension between Astrid and Cicero eventually boils over. After the quest "Breaching Security," Cicero loses his mind when Astrid continues to ignore the Night Mother’s commands. He attacks several members, including Arnbjorn, and flees. This triggers "The Cure for Madness," which is the most critical Cicero-related quest in Skyrim.

1. Search Cicero’s Room for Clues

Astrid directs you to search Cicero’s quarters in the Falkreath Sanctuary. You are looking for his journals. While there are five volumes in total (which we highly recommend reading for the lore), the final volume is the one that progresses the quest. It reveals the existence and password of a hidden, abandoned sanctuary in Dawnstar.

2. Obtain Shadowmere

Before you leave, Astrid gives you Shadowmere, the legendary Dark Brotherhood horse. Shadowmere emerges from the black pool outside the sanctuary. This horse is not only visually striking with its glowing red eyes but also has incredibly high health regeneration, making it one of the best mounts for combat in the game.

3. Arrive at the Dawnstar Sanctuary

Travel to the northern coast near Dawnstar. Outside the entrance to the sanctuary, you will find Arnbjorn, wounded but alive. He tells you he managed to strike Cicero but was injured in return. He warns you that the jester is "faster than he looks."

4. Navigating the Dawnstar Sanctuary Traps

The interior of the Dawnstar Sanctuary is designed to keep intruders out. It is filled with Sanctuary Guardians—ghostly assassins who use leveled gear.

  • The Spear Trap: Early on, you’ll cross a bridge. Stepping on the pressure plate triggers a spear trap. We recommend using "Become Ethereal" or simply sprinting across.
  • The Udefrykte: In the ice tunnels, you will encounter a unique frost troll named Udefrykte. This is a callback to The Elder Scrolls IV: Oblivion. It hits hard and has a high health pool. Use fire-based spells or enchantments to negate its health regeneration.
  • The Skill Books: Don't miss the archery skill book The Marksmanship Lesson and the one-handed book Fire and Darkness found on a table near the spiral stairs.

5. Confronting Cicero

As you progress, Cicero’s voice echoes through the halls. He mocks you, taunts you, and eventually begs you to listen. When you finally reach the inner sanctum, you find him lying on the floor, seemingly mortally wounded.

Should You Kill or Spare Cicero?

This is the moment that defines your playthrough of the Dark Brotherhood questline. Cicero is on the floor, claiming he is too weak to fight. You have a choice: follow Astrid’s orders to kill him, or walk away and spare his life.

Option 1: Kill Cicero

If you choose to execute him, the process is straightforward. However, be warned: as soon as you strike him, he may jump up, revealing that he was faking the severity of his injuries to test your resolve.

  • Rewards: You can loot his unique "Cicero’s Outfit."
    • Cicero's Hat: Sneak is 35% better.
    • Cicero's Clothes: Prices are 20% better, One-handed damage increased by 20%.
    • Cicero's Gloves: Double sneak attack damage with one-handed weapons (stacks with Backstab perk).
    • Cicero's Boots: Wearer moves silently (Muffle).
  • Narrative Outcome: Astrid is pleased, and the Brotherhood continues on its path toward the finale.

Option 2: Spare Cicero

If you choose to leave the sanctuary without killing him, you must return to Astrid and lie, telling her the deed is done.

  • Rewards: You do not get his specific outfit immediately, but a slightly weaker version ("Jester’s Outfit") can be found on a table at the entrance of the Dawnstar Sanctuary.
  • Narrative Outcome: Cicero survives. After you complete the final quest of the main Dark Brotherhood line ("Hail Sithis!"), Cicero will reappear at the Dawnstar Sanctuary.
  • Recruitment: He will express his gratitude for your mercy and offer his services as a permanent follower.

Why We Recommend Sparing Him

From a pure gameplay perspective, sparing Cicero is the superior choice.

  1. The Follower Stats: Cicero is one of the strongest followers in Skyrim. He has a level cap of 100 (most followers cap at 50) and has 100 in Sneak, One-Handed, and Light Armor.
  2. Unique AI: He is one of the few followers who will spontaneously dance or perform when idle.
  3. The Lore Factor: Sparing him feels more aligned with the "Listener" role. As the Night Mother’s chosen, protecting her Keeper makes more sense than following the orders of Astrid, who eventually betrays the Brotherhood.

Cicero as a Follower: Combat and Utility

If you spared him, you can find him hanging around the Dawnstar Sanctuary after the "Hail Sithis!" quest is completed. Here is a breakdown of why he is a top-tier companion.

Combat Prowess

Cicero is an assassin. He excels at using daggers and one-handed swords. Unlike many followers who bumble into traps or alert guards, Cicero’s high Sneak skill makes him ideal for players who prefer a stealthy approach. In our testing, he rarely triggers pressure plates and is very effective at initiating sneak attacks alongside the player.

Essential Status

Cicero is flagged as "Essential" once he becomes a follower. This means he cannot be killed by enemies or by your own stray arrows/spells. He will simply take a knee when his health reaches zero.

Dialogue and Personality

One of the main reasons players choose Cicero is his dialogue. He has hundreds of unique lines of dialogue for almost every location in Skyrim. Whether you are in a Dwemer ruin or a bustling city, Cicero will have a snarky, insane, or insightful comment to make.

The Tragic Backstory: What the Journals Reveal

To truly understand the Cicero questline, you must read the five volumes of Cicero's Journal found during "The Cure for Madness." They chronicle his life from a sane, successful assassin in the Cyrodiil branch of the Brotherhood to the madman he is today.

  • The Last Contract: Cicero’s madness began after he killed a famous Jester. He became obsessed with the kill, eventually taking on the persona of his victim to cope with the isolation of being the last member of his sanctuary.
  • The Duty of the Keeper: The journals describe the agonizing years he spent as the Keeper of the Night Mother, waiting for a Listener to be chosen. The silence of the Night Mother is what ultimately broke his mind.

Understanding this backstory turns the quest from a simple "kill the traitor" mission into a nuanced story about the weight of religious burden and the loss of identity.

Frequently Asked Questions (FAQ)

What is the difference between Cicero's Outfit and the Jester's Outfit?

Cicero's Outfit is a high-level version of the Jester's Outfit. While they look identical, Cicero’s gear has significantly higher percentage bonuses (e.g., 20% One-handed vs. 12% for the Jester version). If you want the best stats, you must kill him; if you want the follower, you keep the Jester version.

Can Cicero be married?

No. In the vanilla version of Skyrim, Cicero is not an available marriage candidate, regardless of how much he likes you or if you wear an Amulet of Mara.

Does sparing Cicero affect the "Destroy the Dark Brotherhood!" quest?

No. The "Destroy the Dark Brotherhood!" quest is triggered by killing Grelod the Kind and then attacking Astrid in the abandoned shack. If you are already on the path of completing Cicero's quests, you are committed to the Brotherhood's side.

Is Cicero actually injured when you find him in Dawnstar?

In terms of game mechanics, no. If you attack him, his health bar is full, and he will fight back with full vigor. He is using his deceptive nature to see if the Listener will actually carry out Astrid's "unholy" order.

Summary of the Cicero Quest Experience

The Cicero questline in Skyrim is a masterclass in character writing. From the "Delayed Burial" encounter to the final choice in the "Cure for Madness," every interaction with this jester is designed to make you question the morality and traditions of the Dark Brotherhood.

While killing him offers immediate gratification and some of the best stealth gear in the game, sparing him provides a deep, mechanical advantage in the form of a level-100 essential follower and a more "lore-accurate" conclusion to the Listener’s journey. Whatever you choose, make sure you take the time to read his journals—they transform a "crazy NPC" into one of the most tragic figures in the Elder Scrolls lore.