Boosting pickpocketing

[craig234]

I just got to a situation to have Astarian pickpocket, and would like to boost his rolls if I can. What are some good ways? Spells, potions?

[ahsanford]

Enhance ability --> cat's grace --> advantage on your DEX roll
Guidance --> +1d4 on your roll
Bardic inspiration --> +1d6/1d8/1d10 on your roll
Gloves of Thievery (act I item at Zhentarim hideout store)--> advantage on your dex roll
(and I'm guessing there are 2-3 other things you can do, folks will speak up)

And these bonuses + advantage can stack.

Unlike a dialogue, where you do this at the last minute, I think you need to do all this in advance of getting in position and going for the take.

Spells and potions generally won't help the take, but may help your escape --> improved invisibility will help you sneak away from the target if they call guards to assist them.

- A

[craig234]

Thanks. Is invisibility better than just hiding in shadows? Does pickpocketing break it?

Does the stealth bonus from 'pass without trace' help pickpocketing rolls?

[Nordil(Hun)]

Originally posted by craig234:

Thanks. Is invisibility better than just hiding in shadows? Does pickpocketing break it?

Does the stealth bonus from 'pass without trace' help pickpocketing rolls?

Invisibility is broken when you pickpocket.(Or should.)
Two different skills. Stealth and pickpocket are different.

You can also debuff the person you are trying to steal from, but you need to do it in a way he does not notice it.
Also the roll shown is the roll you need for succeses. For some reason Larian added a completely different dice showing system for pickpocket only.

[アンジェル]

Originally posted by craig234:

Boosting pickpocketing
I just got to a situation to have Astarian pickpocket, and would like to boost his rolls if I can. What are some good ways? Spells, potions?

The best is truly the gloves which give advantage on Sleigh of Hand. You can equip them and unequip them at your convenience without the need for "fixed adjustments". Otherwise ahsanford has covered everything quite thoroughly and nicely.

Originally posted by craig234:

Thanks. Is invisibility better than just hiding in shadows? Does pickpocketing break it?

Does the stealth bonus from 'pass without trace' help pickpocketing rolls?

Invisibility in general breaks when making an action. Pickpocketing counts as action. There is also Greater Invisibility.

Pass without Trace explicitely says it helps with Stealth checks, and therefore only stealth checks.

[Popsicles]

Originally posted by craig234:

Thanks. Is invisibility better than just hiding in shadows? Does pickpocketing break it?

Does the stealth bonus from 'pass without trace' help pickpocketing rolls?

I use invisibility in crowded areas, like at Damon's shop when he gets to BG. Doesn't affect the sleight of hand roll, but lets you auto-stealth.

[EricHVela]

"Greater Invisibility" lets you do actions (including attacks) and stay Invisible with passing Stealth checks. Each action increases the difficulty of the next Stealth check. You can lockpick and stay Invisible by passing the Stealth check. Things that improve Dexterity and Stealth bonuses make staying invisible easier.

[craig234]

Do subsequent pickpockets on the same person get harder or stay the same?

[ahsanford]

The gloves are the single most useful item of my playthrough. It’s better than melee-advantage-all-day items, IMHO.

- A