The Pickpocket skill allows you to steal items off of a person. As perks are gained in this skill, you gain abilities that make pickpocketing attempts more likely to succeed, silently kill people with poisons, increase your maximum encumbrance, and the ability to steal equipped items. The Pickpocket skill tree has a total of 8 perks, requiring a total of 12 perk points to fill.
In-game Description: The stealthy art of picking an unsuspecting target's pockets. A skilled pickpocketer is less likely to be caught and is more likely to loot valuables.
 Skill Perks
|Perk||Rank||Description||ID||Skill Req.||Perk Req.|
|Light Fingers||1||Pickpocketing bonus of 20%. Item weight and value reduce pickpocketing odds.||000be124|
|2||Pickpocketing bonus of 40%. Item weight and value reduce pickpocketing odds.||00018e6a||20 Pickpocket|
|3||Pickpocketing bonus of 60%. Item weight and value reduce pickpocketing odds.||00018e6b||40 Pickpocket|
|4||Pickpocketing bonus of 80%. Item weight and value reduce pickpocketing odds.||00018e6c||60 Pickpocket|
|5||Pickpocketing bonus of 100%. Item weight and value reduce pickpocketing odds.||00018e6d||80 Pickpocket|
|Night Thief||+25% chance to pickpocket if the target is asleep.||00058202||30 Pickpocket||Light Fingers|
|Cutpurse||Pickpocketing gold is 50% easier.||00058204||40 Pickpocket||Night Thief|
|Keymaster||Pickpocketing keys almost always works.||000d79a0||60 Pickpocket||Cutpurse|
|Misdirection||Can pickpocket equipped weapons.||00058201||70 Pickpocket||Cutpurse|
|Perfect Touch||Can pickpocket equipped items.||00058205||100 Pickpocket||Misdirection|
|Extra Pockets||Carrying capacity is increased by 100.||00096590||50 Pickpocket||Night Thief|
|Poisoned||Silently harm enemies by placing poisons in their pockets.||00105f28||40 Pickpocket||Night Thief|
 Skill Usage
The chance of successfully pickpocketing an item is computed as follows: [verification needed — see]
|Factor||Effect on pickpocket chance|
|Pickpocketer's Pickpocket skill||+1% per point|
|Target's Pickpocket skill||-0.25% per point|
|Pickpocketer is hidden||+25%|
|Item's gold value||-0.1% per point|
|Item's weight||-4% per point|
|Perks||add the perk percentage|
|Alchemy||multiply chance by 100% + total alchemy bonus percentage|
|Enchantments||multiply chance by 100% + total enchantment bonus percentage|
The maximum chance for success is 90%.
The maximum amount of gold pickpocketable on an awake target is 3,102 (1% chance on a 15 Pickpocket skill target). 1,500 of this comes from perks. The most you can steal with maximum chance (90%) of success is 2,212. Alchemy and Enchantments will increase the chances of a successful Pickpocket, but will not allow you to pickpocket more gold at small chances.
After investing in the Poisoned perk you can reverse-pickpocket poisons onto targets to damage them. Giving multiple poisons to a target will make them "take" the poisons until they are either all gone or the target dies. Remaining poisons will be left on the corpse and are retrievable.
If you fail, the target will detect you and you may receive a bounty, if you are detected by someone that reports crimes. Even if successful, there is also a chance that the target will hire thugs to kill you.
 Skill Increases
 Character Creation
The following races have an initial skill bonus to Pickpocket:
- +1 Pickpocket reward (as well as +1 to all other stealth skills) from Inge Six Fingers (Bards College) for completing the quest Finn's Lute.
- +5 Pickpocket reward (as well as +5 to all other stealth skills) by selecting "The Path of Shadow" from the Oghma Infinium after completing the quest Discerning the Transmundane.
 Gaining Skill XP
- Pickpocket skill gains are based on value of stolen items.
- Training Pickpocket must be planned carefully, as it levels extremely fast, potentially advancing your character level too far at low levels.
- Easy ways of training your Pickpocket skill include:
- Stealing jewelry; high success rate (low weight), big skill gains (high value).
- Trainer pickpocketing: Pay a trainer to train a skill, steal your gold back, pay again, and repeat for as long as you're able to "buy" new levels of training. This way, you can gain as many levels of the skill as you wish to learn from the trainer, and gain levels of Pickpocket with a net cost of 0 gold. With a high Pickpocket skill, you can train up to level 51 without Pickpocket perks, or to 76 with all of the perks. After this, the gold cost becomes too expensive to pickpocket back. This is an extremely efficient method of leveling Pickpocket to the low 50s; at 15 skill with 1 perk, you have a 51% chance of stealing back your training fee, which goes up to 71% when you reach level 20 and invest another perk, and you will gain several extra levels of pickpocket each time you steal back your fee. Be warned that at low levels this method can cause you to level up repeatedly, making combat more difficult.
- Reverse pickpocketing: Reverse-pickpocket gold onto someone and steal it back. The bound NPCs found during the quest With Friends Like These... will not report you for any crime for the duration of the quest and are thus excellent targets. This is a good method if your Pickpocket level is over 90. 1500 gold is a good amount to do this with if you have the Cutpurse perk. Store the rest of your gold somewhere before doing this.
One achievement is related to Pickpocket:
- There is a maximum percentage chance to steal displayed in game of 90%.
- The Misdirection and Perfect Touch perks will only work if you are attempting to pickpocket while not detected by your target. It is sometimes possible to steal equipped items while still being "detected" by a different NPC.
- After unsuccessfully attempting to pickpocket an NPC, the NPC cannot be pickpocketed again for 2 days. The NPC will not reset if the player waits two days in the same room. This can also be reset if your unsuccessful attempt causes you to be approached by a guard and you are able to make them go away quietly (Bribe, announcing your "status", or paying them as "part of the Guild".) A third solution is available to master Illusionists; casting Harmony will cause all affected targets to "forget" if they have been pickpocketed recently. This does not work with other Pacify spells.
- The Cutpurse perk says "Pickpocketing gold is 50% easier". This can be a little misleading, as the bonus you gain can be much higher than half of your "chance to steal". What it actually means, is that Cutpurse adds the number 50 to your "chance to steal", although the number will still max out at 90%. At Pickpocketing level 100, trying to steal 1250 gold from an NPC trainer increased from 6% to 56% with the Cutpurse perk.
- Reverse pickpocketing a poison using the Poisoned perk does not count as a crime, even if the magical effect of the poison (e.g. "damage health") would otherwise be considered a criminal act if applied any other way. This makes it entirely possible to kill or weaken innocent enemies, right in front of everyone, without incurring a bounty.
- After taking Rank 5 of the Light Fingers perk, instead of raising the stealing chance, this perk can instead drop it to zero when trying to steal large amounts of gold (around 1600-1700). For example, if you use a trainer to train Archery from 57 to 58, you can use Pickpocket to get your money back. When you have Rank 4 of the Light Fingers perk, the odds are about 62%, but if you take Rank 5, they suddenly drop to zero.
- This bug is fixed by version 1.1 of the Official Skyrim Patch.
- Fortify Pickpocket bonuses from apparel and potions may reduce your pickpocketing chance rather than increasing it.
- This bug is fixed by version 2.0.0 of the Unofficial Skyrim Patch.
- The odds of pickpocketing may change when you scroll through the items in an NPC's inventory; therefore, it is sometimes better to scroll through the inventory until the displayed chance for the item you want to steal satisfies you the most.
- On rare occasions, you may be unable to pickpocket any NPC in an area with no clear cause, instead receiving the message you normally see when trying to pickpocket someone who has already caught you. Waiting 48 hours in a different location seems to fix this issue.
- If you save before pickpocketing, and reload after you are caught, you may continue to hear people yelling at you for pickpocketing, even though they're perfectly friendly when you talk to them. This will continue until you leave the area.
- Sometimes when you get caught pickpocketing, the target will attack you, but the guards won't attempt to arrest you.