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Wield nimble fingers. Steal stuff.
Sleight of Hand is a Dexterity skill. It helps you pick locks, pick pockets, and disarm traps. The higher your Dexterity score, the more likely you are to succeed on Sleight of Hand ability checks.
Proficiency
Characters who are proficient in Sleight of Hand can add their proficiency bonus when making ability checks.
The following backgrounds grant proficiency in Sleight of Hand:
The following classes can choose to select Sleight of Hand as a proficient skill at Level 1:
- Bard
- Rogue
- Ranger, via the Natural Explorer option Urban Tracker
Uses
- Picking locks (requires Thieves' Tools).
- Disarming traps (requires Trap Disarm Toolkit).
- Pickpocketing from NPCs.
- Stealing items without being noticed (see also Stealth).
Pickpocketing and stealing tips
Picking pockets and stealing items in crowded areas can be difficult due to NPCs in the area having overlapping sight cones or moving around. A trick around this is to use your party members to start conversations with the NPCs that are causing you trouble. Typically the NPC will turn to face the party member they are in a conversation with and thus you can turn their sight cone away from the mark you are intending to pickpocket or the item you wish to steal. This can also be used to hold an NPC still while you attempt to pickpocket them.
Another technique to pickpocket in crowded areas is to go Invisible first. If you're invisible, you will always successfully Hide, which will let you attempt to pickpocket even in a crowded room. You will be seen as soon as you pickpocket one item, though, as Invisibility will drop (unless you cast Greater Invisibility, which just has a chance to drop). However, if you quickly go invisible again, or Go to Camp, the NPC you stole from won't be able to find you to accuse you of stealing. You can use this to slowly clear out the inventory of an NPC in a crowd.
An additional technique is to fire an Arrow of Darkness near an NPC to surround them in the cone of darkness, activating turn-based mode, Cunning Action: Hide and then begin your pickpocket attempts. In some scenarios, you may have to pass a Stealth Check, but in most scenarios, this will allow an easy pocket.
The maximum DC of a pickpocket attempt is 30, so if you build up your Sleight of Hand bonuses high enough, it's possible to make even the most difficult pickpocket attempts always succeed. To do this, get your Sleight of Hand bonus to +8 from Expertise, +6 from Dexterity (using The Graceful Cloth, feats, and/or various permanent bonuses to reach 22 Dexterity), and +4 from Unlucky Thief's Gloves and Smuggler's Ring, for a total bonus of +18 displayed in the character sheet. Then add +2d4 from Guidance and Shapeshifter's Boon Ring, and be a level 11 Rogue with Reliable Talent, so you can't roll below 10. This makes the target roll in the pickpocket interface max out at 12 (DC 30 - 18 = 12), which you can't fail because you'll never roll below 10, and you'll get at least +2 on top of that from the d4s.
Related items
+1 to ability checks
+2 to ability checks
+1d4 to ability checks while shapeshifted
Advantage on ability checks
Advantage on all Dexterity checks
Related spells
- Grants Proficiency in all Skills of a chosen Ability.
- Grants Proficiency in all Dexterity Skills.
- Grants a 
+1d4 bonus on all Skill Checks.
- Grants Advantage on all Dexterity Checks.
- Grants Disadvantage on all Dexterity Checks.- Bardic Inspiration - Grants a +1d6/+1d8/+1d10 bonus on all Skill Checks.