Smuggler's Run

Background
Upon entering the City of Amaranthine for the first time you will come to a NPC called shady character. he will begin talking to you about your reputation, if you're interested you can follow him and speak with him further. there are 2 distinct paths you can take with this quest line. you can help the smugglers or you can help the city blue snoogles only choose one side. If you choose to side with the smugglers you get an extra person to fight at Vigil's Keep for you, but the guards call you a murderer and treat you rudely. Choosing the smugglers is also the only way to get a key into the guard house in Amaranthine. Note that doing a SINGLE quest, even the bartender quest for the smugglers, will prevent you from EVER siding with the guards, PERIOD.

Upon talking with the shady character he will tell you there has been some trouble with trade in the city, through his help and the other smugglers you will be entitled to a cut if you help out. continuing talking with the shady character you will learn he wants a small favor, the local bartender has a secret passage and he is trying to extort more coin. The smugglers want you to persuade or intimidate him to open the passage. After dealing with the bartender and speaking again with the shady character you will learn that there are some Thief's that are getting in the way and if you will deal with them you can earn more money.

Upon speaking to the smuggler leader he will thank you for your assistance in dealing with the unwanted guests, Continue talking with him about why he is down in these caves you find out he and his men are responsible for bringing goods and supplies into the city for the people in need. He will then ask you to do one more favor for him, The city guard has been causing problems he wants you to take care of the Lieutenant. He will tell you the Lieutenant should be in the Guard house and one of the city guards around the city should have the key.

After obtaining the key to the guard house and dealing with the lieutenant you will find another key that leads to a cell door on the opposite side of the guard house. In which you will find Jacen, An Elf that claims to be the Finest archer in the whole arling, If you release him you can have him fight at Vigil's Keep for you.

Walkthrough
This walkthrough will assume you want to help the smugglers, if you want to help the city guard then see the quest guide for Law and Order.

You can find the NPC named Shady Character to the left of the gates when you arrive at Amaranthine.

Head over to The Crown and Lion Inn and have a chat with the bartender. After you persuade or intimidate him to open the hidden passageway, head back to the Shady Character. After speaking with him, enter the house he's standing next to, and go into the passageway. Upon entering the secret door you will have to fight a bunch of thieves. After defeating them, a group of smugglers enter. Speak to the Smuggler Leader.

After talking with him, head out of the caves (the easiest way is to exit the other side of the cave from where you entered) and you will find yourself inside the Crown and Lion Inn. Find your way to each of the doors to the battlements (they will have quest markers). One of the sergeants will have the Guard House key. Upon looting the key the quest will update. On the north side of the city you will find a door that leads to the Guard House; use your key to enter.

Upon entering you will be confronted by the Lieutenant. You will need to fight him and his men. After killing the Lieutenant and his allies loot his body to find a cell key. Go around to the back of the guard house and open the cell door there. Jacen, an elf, is locked up in a cage. If you choose to release him he will gladly head to Vigil's Keep and fight for you. When you are done dealing with Jacen, collect loot from the various chests and head back to the Smuggler Leader.

After speaking with the Smuggler Leader for the last time the quest will be completed.

Result
First reward: 10 gold, a key to the secret door in the house next to shady character

Second reward: 15 gold, Nathaniel disapproves -1

Final reward: 20 gold, Landsmeet Shield.

Exploit/Glitch/Bug
After the second quest (killing the thiefs), you can speak to the smuggler's leader to receive 15 Gold. If you do not accept his third quest and speak to him again, you again receive 15 Gold and some experience. This is an early way to level up characters as much as you wish. (PC)

also if you talk to the main guard about the smuglers problem(law and order quest) you will lose the ability of completing the quest which can also infect the other quest since the bar keeper will still talk to you and open the door,but the guards wont like that and you will be stuck with both quests undone.