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"Elder Scrolls V: Skyrim" Pickpocket Guide: Tips and Tricks for Better Pickpocketing

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Christine has been playing Skyrim for over a decade and has built many characters over the years

Skyrim Pickpocketing, an Underrated Skill

For some, pickpocketing in Skyrim can be tedious and boring. But I believe pickpocketing can be fun after the initial few levels. You can use the pickpocket skill to level up quickly, make a lot of gold, disarm opponents, and kill enemies stealthily.

Here is a comprehensive guide on perks, leveling up, pickpocketing strategies, and assassination strategies.

Note: No mods are used, just basic Skyrim Special Edition.

Which Race Is the Best for Pickpocketing?

Is there a best race for pickpocketing in Skyrim?

The answer is both yes and no. Why? Because while a race like Kajit starts out with the highest pickpocket and sneak levels, the advantage is very small, and it only helps a little at the beginning of your game.

A Kajit starts out with a pickpocket level of 20, and a sneak level of 25. This is higher than other races, but the advantage is small and doesn't last long.

For instance, both an Imperial, with a sneak level of 15, and a Kajit have about the same chance of a successful pickpocket attempt while sneaking with the eye closed (about 55%) at level one with no perks. The Kajit only has a slight advantage (30% ) compared to the Imperial (25%) with the eye partially open.

So from my experience, it doesn't really matter what race you chose, it is just a little quicker to level up sneak and pickpocket with the Kajit.

Perk Tree

The perk tree for pickpocket is straightforward and simple. There are eight total perks, with the first perk, Light Fingers, taking five perks to fill. All other perks take one.

  • Light Fingers: The Light Fingers perk is the bottom perk in the tree, leading to Night Theif. There are a total of five perks to fill, each preceding the next. Odds are reduced for value and weight, with bonuses at 20, 40, 60, 80, and 100. Skill requirements are 15, 20, 40, 60, and 80.
  • Night Theif: This perk gives a 25 percent chance bonus to pickpocket sleeping targets. The skill requirement is level 30. Leads to Poisoned, Cutpurse, and Extra Pockets.
  • Poisoned: Gives the ability to hurt your enemy by placing poison in their pocket. The skill level requirement is 40.
  • Extra Pockets: You increase your carrying capacity by 100. Takes a skill level of 50 to reach this perk.
  • Cutpurse: It makes it 50 percent easier to pickpocket gold. The skill level requirement is 40. Leads to the Keymater and Misdirection perks.
  • Keymaster: This perk allows you to pickpocket keys more easily. The skill requirement is 60.
  • Misdirection: You can now pickpocket equipped weapons, to sell or to disarm enemies. Your skill level must be 70 to get this perk. Leads to the Perfect Touch perk on the tree.
  • Perfect Touch: The top skill in the tree, which takes a skill level of 100 to reach. This perk allows to pickpocket equipped items, such as clothing and armor.

Does Sneaking Help Your Pickpocket Success?

Yes, it does in a lot of cases. Of course, you must be in the sneak mode to pickpocket, but does having the eye closed help in your success? It does, and here is a breakdown of the first three perk points into Light Fingers.

  1. Light Fingers Level 1: About 75% chance of success for non-expensive items with the eye closed, and 50%chance with eye partially closed.
  2. Light Fingers Level 2: About 90% chance with non-expensive items, and 50% chance with expensive items, with the eye closed. About 70% chance for non-expensive items, 25% chance with expensive items, with the eye partially open.
  3. Light Fingers Level 3: About 90% chance with non-expensive items, and 85% chance with expensive items, with the eye closed. About 90% chance with non-expensive items, and 60% chance with expensive items, with the eye partially open.

So you can see being in sneak mode with the eye fully closed does help, and it gets progressively better with higher levels and added perks.

Skill Trainers

There are two pickpocket skill trainers in Skyrim: one expert, and one master trainer.

  • Silda the Unseen: Silda is an expert trainer, located in Windhelm. She can train you up to level 75. She is a beggar dressed in rags, often found in the graveyard, or warming her hands at a firepit outside Candlehearth Hall.
  • Vipir the Fleet: Vipir is a master trainer, located in the Thieve's Guild Cistern. He can train you up to level 90. You have to first become a member of the Thieve's Guild to buy his training services.

Potions and the Deft Hands Enchantment

Pickpocketing potions and items enchanted with Deft Hands will help raise your chances of success.

For creating potions, mix two of these items at an alchemy lab:

  • Blue Dartwing
  • Orange Dartwing
  • Nordic Barnacle
  • Slaughterfish Egg

You can also find Pickpocket Potions throughout Skyrim to buy, loot, or steal.

You can also use jewelry, armor, or clothing enchanted with Deft Hands. These can be found, bought, created at a smithing forge, and enchanted at an enchanting table. From my experience, I find that buying one or two items is sufficient for a boost while pickpocketing higher value or harder to steal items.

Assassination By Reverse Pickpocketing

Assassination by pickpocketing is simple. You just need to sneak up to an enemy and reverse pickpocket a poison into their inventory. You can do this at any level, even with no perks in sneak or pickpocket.

I like to use poisons such as Slow made using River Betty, Deathbell, and Lingering Damage Health. Lingering Damage Health is my favorite, as it is the strongest poison I know of with the most damage to health.

Slow is my second choice, as it does a lot of damage if you specifically use the combination of River Betty and Death Bell. Other combos won't work for damage.

For Lingering Damage Health, use any combination of:

  • Orange Dartwing
  • Mora Tapinella
  • Slaughterfish Eggs
  • Slaughterfish Scales
  • Imp Stool

If you are playing on Legendary, it's going to take strong potions, or a lot of them used successively. My favorite strategy is to build Lakeview Manor once I reach Level 9 and include the garden and greenhouse. This way I can plant Deathbell, Imp Stool, Mora Tapinella, and other useful ingredients and have a steady supply. I will then regularly collect other ingredients I can't grow such as River Betty. I usually collect these at the Riften Fishery and docks.

You can also paralyze an enemy. I use a combination of Canis Root and Imp Stool, or Canis Root and Swamp Fungal Pod for my Paralysis Poison.

Who can you assassinate with this method in Skyrim? Only enemies that you have the ability to pickpocket, and only in non-combat situations.