What is the highest minimum and maximum roll possible on a (Dex) sleight of hand/pickpocket check? [closed]


FOR THE KLEPTOMANIACS OUT THERE:

Let’s say we’re attempting to pickpocket something from someone and would like to reduce our chances of failure as much as possible. What is the highest minimum roll and maximum roll reliably possible in the game? In order to make this easier to replicate for others, I’m going to offer some restrictions:

  • Things that are not largely guaranteed in most games, such as: Boons, Artifacts, and Manuals.
  • This can be any level character up to 20th level, all that matters is that it still remains the highest min and max roll for the check.
  • Must be acting alone and receive assistance only from themselves, their items, feats, racial abilities, class features, etc.

These restrictions should ensure that the check can be performed reliably any time it is made by anyone with the proposed build in nearly any campaign with the average amount of magical items and quest rewards, etc.

I will post my own findings as an answer below. Feel free to use it as a frame for further answers, or offer one all your own.

Can a Thief rogue disarm an enemy in combat using Sleight of Hand as a bonus action?

One of my players rolled a Thief rogue. At level three they get the Fast Hands feature:

You can use the extra action granted by your Cunning Action to make Dexterity (Sleight of Hand) checks, use your thieves’ tools to disarm a trap or open a lock, or use an object in the environment.

The player asked mid-fight to use a Sleight of Hand check to disarm a foe. Since this isn’t clear in the PHB, the discussion slowed down the fight considerably. To end this discussion, I ruled that the player could make a Sleight of Hand check contested by the enemy’s Strength (Athletics) check.

I still find it hard to see how a Sleight of Hand check could work to disarm mid-combat, since there’s no way you’d be able to "sneakily" take someone’s weapon out of their hands while fighting.

There is an optional "Disarm" rule as listed in the DMG, which uses a weapon attack against an adversary’s Dexterity (Acrobatics) or Strength (Athletics) check to determine whether or not a disarm action succeeds.

Could a Thief rogue disarm an enemy in combat using Sleight of Hand as a bonus action?

When stealing something do you need to roll stealth and sleight of hand?

Scenario: An arcane trickster casts disguise self as a blind old man.

In a crowded room, his accomplice distracts the target, while the arcane trickster tries to steal his pouch of gold. As a DM, what would you have him roll?

I am trying to solve a minor disagreement between a player (me) and a DM. He felt like I should roll a stealth check followed by a sleight of hand check. I thought I should roll a sleight of hand check with advantage since I had gone to all the trouble to orchestrate the distraction with a party member and disguise myself.