Quick Walkthrough
- Speak to Cicero on the road leading to Loreius Farm.
- Speak to Vantus Loreius at the Loreius Farm.
- Make your decision:
- Persuade Vantus Loreius to fix the wheel.
- Turn in Cicero to the wandering guard.
 Quest Conflicts
Beginning Innocence Lost or With Friends Like These... will create some minor restrictions on your options in this quest. Entering the Dark Brotherhood Sanctuary or starting Destroy the Dark Brotherhood! will cause this quest to fail. However, none of these contingencies are of significant consequence to progression through the Dark Brotherhood questline or through the game in general, as this quest is a relatively minor one.
 Detailed Walkthrough
 Stranded Jester
On the road north of Whiterun and near Loreius Farm, you will encounter a very odd jester named Cicero. He claims that he is from Cyrodiil and is moving to Skyrim. His wagon, which he says contains the remains of his mother, has broken down by the roadside. He asked Vantus Loreius, the owner of the nearby farm, to help him fix his wheel, but Loreius refused. Cicero will ask you to convince Loreius to help him so he can move on.
Speaking to Vantus Loreius will reveal that he was unwilling to help because of Cicero's odd behavior, and he speculates that Cicero's box likely contains Skooma or other illegal cargo, and doesn't want to chance aiding him in any illicit activity. Vantus asks that you convince a patrolling guard—either a Roadside Guard or Pale Hold Guard—to arrest Cicero.
 Helping Cicero
To help Cicero, you can persuade Vantus to do the right thing and fix the wagon wheel. It is an easy speech check. Vantus will reconsider and promise to help Cicero on his way. After you notify Cicero, he thanks you and gives you a certain amount of gold depending on your current level.
 Turning in Cicero
To turn in Cicero, you need to find the guard that patrols the roadway near the farm. He patrols very close to the wagon and is frequently within sight of the wagon. The guard will place Cicero under arrest. Cicero promises to make Loreius pay and chastises you for not being of assistance. After notifying Vantus, he thanks you for bringing him peace and gives you gold.
Cicero is an assassin and the Keeper of the Dark Brotherhood. The coffin he is transporting contains the remains of the Night Mother. Choosing to help Cicero will lead to him showing gratitude if you join the Brotherhood. If you turn him in and later return to the farm, you'll find that Vantus Loreius and his wife, Curwe, have been slaughtered (although if you wait too long the bodies will be gone). A passing guard will remark "You don't want to go up there, citizen. It's a terrible sight. The farmer and his wife murdered in the middle of the night. So many knife wounds." If you later join the Dark Brotherhood, Cicero will be slightly upset with you for not helping him. Whichever attitude he shows toward you will carry no practical implications if you join the Brotherhood.
Regardless of how you resolve the quest, you get the same amount of gold:
- The quest can be initated not only by encountering Cicero, but also by overhearing a conversation between Uthgerd the Unbroken and Skulvar Sable-Hilt in front of the Whiterun Stables when you go there for the first time. That adds the quest and sets it to stage 5.
- If you do not interact with Cicero prior to joining the Dark Brotherhood, there will be alternate dialogue options when you meet him in the Falkreath Dark Brotherhood Sanctuary.
- Even after you've convinced Loreius to help, Cicero and his broken wagon may remain on the road indefinitely unless you join or destroy the Dark Brotherhood, in which case he will move on regardless of whether you convinced Loreius or not.
 Quest Stages
- The following empty quest stages were omitted from the table: 0, 255.