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An additional technique is to fire an [[Arrow of Darkness]] near an NPC, activating turn-based mode, [[Cunning Action: Hide]] and then begin your pickpocket attempts. In some scenarios, you may need to pass a Stealth Check, but in most cases, this will allow an easy pickpocket in more crowded areas.
An additional technique is to fire an [[Arrow of Darkness]] near an NPC, activating turn-based mode, [[Cunning Action: Hide]] and then begin your pickpocket attempts. In some scenarios, you may need to pass a Stealth Check, but in most cases, this will allow an easy pickpocket in more crowded areas.


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 (apart from rolling a 1, which is always a critical failure). To do this, get your Sleight of Hand bonus to +8 from Expertise, +6 from Dexterity (using [[The Graceful Cloth]], [[feat]]s, 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.
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]], [[feat]]s, 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.


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