The fastest way to level up the Pickpocket skill in Skyrim may come as a surprise to some players. Pickpocket is not the greatest skill in Skyrim, but it certainly has its uses, especially if players are roleplaying as a member of the Thieves Guild, or they just like placing poison on NPCs, or even stealing the armor that the clueless NPC is wearing.
Players can learn how to level Pickpocket to 100 fast and easily through a tried and tested method that has worked for years. Considering Skyrim is well over a decade old and has been released on multiple generations of consoles, it’s safe to say that Skyrim players know the fast way to level 100 Pickpocket.
Reach Riften
Riften is one of the best cities in Skyrim, even if it is home to the Thieves Guild. However, it’s probably best to be around a guild dedicated to robbery than one like the Dark Brotherhood, who will happily assassinate anyone, provided the coin to do so. Players need to head to Riften, which shouldn’t be a difficult task. Players can get there through fast travel, running to the far right of the map, or purchasing a ride from any city stable from a horse-drawn carriage for a cheap amount of gold.
Once players head to Riften, they can avoid the first-time “visitor’s tax” by noticing that the Riften guard is doing a shakedown. This will then give players unbridled access to the city of Riften, where the Dragonborn will want to hang about near Mistveil Keep.
Get A Bounty And Submit To Jail
Now that players are in Riften, they will want to get a bounty, but not by much. Players can either steal something or assault someone so that the guards come rushing over to talk to the player. Players will want to submit and be taken to jail, where all their items will be confiscated into an evidence chest. At this point, players will want to save their game, as they won’t have the easiest time in escaping.
Players mustn't sleep in the bed to skip time, as this will mean that they are no longer a prisoner, and it will also decrease the skills that they have learned due to their time incarcerated. Players are not looking to escape through secret methods, they must remain a prisoner in the Riften jail for this tactic to work.
Lockpick The Cell, Kill The Guards
Players can look at the table on the right and find a single lockpick that they will need to use to unlock their cell. Since they have technically just escaped prison, the guards will attack them, so players need to kill the 2 guards that patrol the Riften jail. This can be done easily by changing the difficulty to Novice or simply using the weapons available in the guard room.
It’s not a hard battle, but the importance of having a save file or a quicksave is so that if the lockpick breaks, players are not stuck. It’s also important because some players that are less skilled in combat or don’t have the best armor and weapons in Skyrim will not be mercilessly beaten and killed by the guards.
Pickpocket Sibbi Black-Briar
Now that the player has escaped, and the guards have been taken care of, it’s time to embark on the most important aspect of the journey, Sibbi Black-Briar. Sibbi Black-Briar is a resident of the Riften Jail, and he is serving a sentence of eight months for murder. Due to his status as a Black-Briar, he has a lovely and comfortable cell, and the way his AI works in Skyrim makes him the perfect target for those that want to reach 100 pickpocket fast in Skyrim.
Since players are technically still a prisoner, their bounty will not increase if they are caught pickpocketing. This means that players can loot things from Sibbi Black-Briar, and if they are caught, they can simply do it again. Sibbi won’t care in the slightest, nor will he respond to failed pickpocket attempts.
To make the process faster, players will want to clear out Sibbi’s pockets of all loot, and then discard it. The best method for pickpocket XP is to throw in a healthy amount of gold by placing it on Sibbi’s person, and then immediately stealing it back.
It’s important that players quicksave for this process, as players will be given a percentage of success for their pickpocket attempt. If players give Sibbi too much gold, then it is very unlikely that they will get it back. Players should start small with the amount of gold they give and take from Sibbi, and then slowly increase it with each pickpocket level increase, as the percentage chance will go up.
It can be a tedious process, to begin with, but players will soon find themselves using pickpocket to great success, with a maximum of 90% success rate in over 200 gold pieces to reach a Pickpocket level faster than just looting every person in Skyrim. The Sibbi Black-Briar method is the most effective and safest way to level up the Pickpocket skill.