Why am I failing pickpocketing?

[Veliponteva]

I have +11 on sleight of hand with 17 dex. yet still after save scumming 10 times to get these cloves from a shop keeper I fail every time.
I went with rogue for being a thief and I can't steal a pair of cloves for the life of me

[Veliponteva]

The target roll is 15 and according to the combat log I roll 20+ yet I fail the pickpocket
How is this????

[OJCOPACABANA]

Because the target roll is what you need to get on the dice roll, after factoring in your modifiers. So if you have a +11 and the target roll is 15, that means the real difficulty class for the gloves is 26. That would mean you need to roll a 15 on the actual die and then your +11 modifier will handle the rest. 15 is unfortunately a pretty decently high roll. You could try turning on karmic dice in the options menu, but I think that will reset on reloading the game so it might not trigger

[Damphair]

Cast guidance on your rogue, I'd recommend to use the gloves of thievery or the robe with cat's grace which gives you advantage on your sleight of hand rolls. If there's a crowd where you might easily get spotted, have your mage cast invisibility. Enter sneak mode when near the target, turn on turn based mode and steal away (quick save after each succesful steal and save-scum your way forward).

You can also split stacks of gold and items into smaller stacks in the trade window, this will lower their respective target rolls.