How exactly does Pickpocket calculate its rolls?

[IIIIIIIIIIIIIIIIIIII]

tl;dr I have a total of a +11 bonus to sleight of hand from all the buffs, items, and also advantage to it from gloves. It shows all these bonuses in the pickpocket menu as a bonus to my rolls.

What I don't understand is how can I have so many bonuses stacked, and still roll under 10 so many times? The game lets you know when it's a critical fail (1) vs if you just failed the roll, and I never try to pickpocket items that require a roll higher than 6, but it still fails more than half of the time.

Are these bonuses not being correctly applied?

[parent child bowl]

Are you reloading after a failed ckeck?

[Orion Invictus]

For whatever reason, the number shown while pickpocketing is the number you need to roll on the d20 to succeed, and not the DC as such.

[talemore]

There's a chance to be caught stealing and there's a chance to steal the item.

[grobdor]

The number shown is the actual d20 odds not DC. if you check the log and look at the raw numbers you'll see what you actually rolled.

[Bongoboy]

As Orion Invictus and grobdor already stated, the number you see in the window is not the DC you have to pass. It calculates all the bonuses in, then shows you what you have to roll on a D20.

I would check, if you have Karmic Dice set to on. Someone on reddit said, what it does is taking a look how often you passed a check and then bends the rolls so you will fail one. If failing means you have to roll a 1 then Karmic Dice will make that happen since it is the only way it can make you fail.

[Raelic]

the pickpocket rolls are based POST modifiers. If it says you need to roll 15, you need to roll an actual 15. This is not the same as other rolls in the game and IMO an oversight.

You can confirm this by checking the sleight of hand entry on your Combat Log after failing or succeeding. You'll see that after all the stagnant bonuses are tallied, it's automatically showing you the number as if it's already included. It won't do it with random bonuses though.

Normally:
The game will show you a 15 Difficulty Chance.
You roll your dice.
The game adds what you get and your modifiers.
The game compares it to the 15 Difficulty Chance.

When Pickpocketing:
The difficulty chance is 21.
You have a +4 bonus.
The game shows you a difficulty chance of 17.
You have to roll a 17 or higher to succeed.

Random bonuses are applied after the roll, however.

You can verify in the combat log checking the sleight of hand entry. I've done it across dozens of save scumming pickpocketing attempts.

[Bongoboy]

Originally posted by Raelic:

the pickpocket rolls are based POST modifiers. If it says you need to roll 15, you need to roll an actual 15. This is not the same as other rolls in the game and IMO an oversight.

There are quite a few things I would call confusing if you not know certain facts. Understanding stealing is one of them.
Maybe I am all alone in this, but if I fail at something multiple times... or I just keep seeing "miss" in combat I want to know how bad I failed. If I know how bad I fail at something I rather try to find out how to raise my odds then keep running headfirst into that wall.