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The Elder Scrolls V: Skyrim Hints
Stealing Tips
1 of 8: As in Oblivion, the game makes it clear when taking an item would be considered stealing. When you aim at a loose item, the word "steal" will show up in red next to its name. When you open a container, any owned items inside it will have their names printed in red.
2 of 8: Remember that people can't see you through solid objects. If you move to where there's a pillar, door, tall counter, or whatever directly between you and everyone in the area who's looking your way, you can snatch anything within reach unseen.
3 of 8: Unlike in Oblivion, using Grab mode to pick up loose items and carry them around won't get you in trouble. If there's an item you want to snatch, but you can't do so unseen, pick it up in Grab mode and drag it off to a spot where you can drop it and then pick it up unseen. (Note that to start dragging an item, you need to face it and lean on the Activate key instead of just tapping it.)
4 of 8: Watch out for people in houses and shops following you around so as to keep you within sight. You'll either have to be very sneaky or move very fast in order to steal their stuff unseen. Or you can try sneaking in and stealing their stuff at night, provided you're able to pick the lock on their door.
5 of 8: Unless you've finished the first two Thieves Guild faction quests, or have the Fence perk for the Speech skill, you won't have anyone to sell stolen items to. Since an item's "stolen" status doesn't ever disappear, not even for equipment items that are improved via smithing or enchanting, you probably won't want to steal anything other than gold coins unless you plan to use it somehow.
6 of 8: As in Bethesda's two recent Fallout games, you won't get in trouble for crouching down and checking someone's pickpocketable inventory if you exit it without trying to take (or give) anything. Also, you don't have to be hidden to successfully pickpocket an item. As long as you beat the random chance that you'll be caught, it doesn't matter if the person you're pickpocketing is looking right at you. But note that if he is, your chance of pickpocketing something successfully will be much lower.
7 of 8: Another pickpocketing note is that many people carry keys to their houses and shops on them. If you pickpocket those keys, and later want to pick the locks that the keys go to (for Lockpicking skill practice), you can put the keys in a container or the inventory of a follower. The game won't let you just drop them for some reason.
8 of 8: Even if you're careful to always quicksave before stealing or pickpocketing something, and quickrestore whenever you're caught, you can still get in trouble for it. There's a one-time random encounter that can happen awhile after you steal something that involves three heavily armed thugs appearing out of nowhere and attacking you. That can be a *serious* problem if your character is still unskilled and low-level, especially if you're playing on a higher difficulty setting. When the encounter happens, run from the thugs and hope you can confuse them by using terrain against them, such as crossing a wide stream. Even then, you'll need to find a spot from which you can kill them with ranged attacks in order to ensure that they don't bother you again. (Note that having a follower or a powerful summoned creature can help a lot.)