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Fallout 3 Hints
Stealing Tips
1 of 7: Unlike in Oblivion, people don't get all upset when you pick up an owned item with the Grab key. So if you want to steal a loose item, but can't do so unseen, pick it up in Grab mode and carry it off somewhere where no one can see you. Go into Sneak mode to make sure you're hidden, then take the item. (You'll still lose karma, but no one will turn hostile or try to reclaim the item.)
2 of 7: Pickpocketing works much the same as in Oblivion, so always quicksave right before you try it and quickrestore if you're caught (and quicksave again when successful).
3 of 7: One difference is that there's no penalty for just looking. You can crouch down and check someone's pickpocket-able inventory in full sight of everyone without getting in trouble as long as you exit the pickpocketing screen without trying to take anything. You can use this to quickly determine who you want to go to the trouble of pickpocketing items from.
4 of 7: You'll get a lot of items from the various towns if you Grab-steal and pickpocket all that you can, especially since new items will appear in people's inventories every now and then. (The same goes for some item containers, too.)
5 of 7: One thing you can do to aid in stealing is to move up against nearby people to push them along. They'll sometimes walk right back to where they were, but usually not. You can use this fact to push someone away from an owned container that you want to loot, or when you want to pickpocket the person without anyone else seeing you do it.
6 of 7: Another thing you can do is wait until well after dark, when most people are in bed. It's a lot easier to pickpocket them and rob their stores and homes then (unless their doors are too tightly locked for you to pick open).
7 of 7: Using a stealth boy can greatly aid you in stealing and pickpocketing unseen, but it's usually not worth using up one of those valuable items for that -- they should mostly be saved for sneaking through dangerous areas (like, say, a deathclaw sanctuary) to retrieve valuable items without having to do any fighting. See the Stealth Boy List to see where all you can find them. Or see the Operation: Anchorage hints in the separate hint file for Fallout 3 game add-ons to learn where to find some special armor with a constant-effect stealth field on it.