So my cousin and i were running through skyrim and my cousin found a great way to easily pickpocket most items in anyones inventory.
so save just before picking someones pocket then enter their inventory while hidden, next take any item that doesnt have a little triangle at the end using the LT or equip button.
We have tried this on dozens of guards in the game with only a level 26 pickpocket and have had around 90% success on each guard.
And if it fails just reload the save and try again. Also dont spam the equip key or the chances of being caught are much higher.
We have tried this ourselves and im wondering if anyone else can test this.