Stealth Tips

A stealthy approach to the game's dungeons and battlefields will let you sneak attack opponents, pick their pockets, or avoid them entirely. While advancing in the arts of the thief will slow your progress a bit (because sneaking around is slower than running), you'll be able to use it to compensate for the overall lower melee damage that you'll likely be dealing due to the fact that you've been working on stealth skills instead of your combat or magical skills.

That said, almost anyone can take advantage of sneaking to deal extra damage, especially when you factor in equipment bonuses.

To Sneak

The basic thief skill is Sneak, which allows you to move around in the game world while remaining hidden from the prying eyes of guards and enemies. When you enter sneak mode, a golden eye will appear around your cursor. Most of the time this will be a bright gold color, which indicates that someone can see you or is otherwise aware of your presence. Your goal is to become hidden, which will turn the icon a translucent grey color.

The point of sneaking? If you stay hidden, then there are all kinds of things that you can do that would otherwise land you in jail or get a pack of guards on your butt. You'll be able to steal items from under the nose of a shopkeeper, pickpocket a guard to nab a key, tresspass through sensitive parts of a castle, or deal huge amounts of damage with a sneak attack.

With a high enough Sneak skill, you'll be able to hide in plain sight.

That said, in order to sneak well, you need to know what factors take part in whether or not a nearby person can see you or otherwise detect you. In no particular order...

Sneak Skill: All characters and creatures in the game have their own Sneak skill ranking, which goes up as they increase in level. (Which, in turn, means that it goes up as you level.) If an enemy has a higher Sneak skill than you do, it'll be more difficult to bypass them or sneak up on them.

Movement Speed: The faster you move, the easier it'll be for enemies to detect you. On the 360, you can move slowly by gently tilting the analog stick.

Light: The more light that's falling on you, the harder it'll be for you to stay out of sight. Keep to the shadows if you want to remain hidden, put away your torches, take off that Light-enchanted ring, etc. Also note that most spells will result in a temporary burst of light when cast, so be careful not to cast them while someone's looking at you. Enemy Line Of Sight: If the enemy you're trying to sneak up on is looking in your direction, you'll have a harder time getting close to them undetected than if you were to approach from their rear.

Weight of Boots: You can sneak in any kind of armor, from regular clothing to heavy armor. However, the heavier your boots are, the more noise you'll make when you move. It's best to go without shoes until you hit Journeyman in Sneak, which eliminates this penalty.

Invisibility: If you have an active Invisibility effect on you, then sneaking is almost child's play, since no one will be able to see you. You'll still make noise, however, which will allow enemies with high Sneak skills to detect you and attack. Even if they don't detect you, you'll lose your Invisibility as soon as you interact with an object or attempt to make an attack, so this is at best a temporary boost.

Chameleon: Chameleon is essentially a less effective form of Invisibility, with differing percentages indicating precisely how concealed you are. The reason it winds up being better than Invisibility is that it doesn't go away when you interact or attack someone; it's more or less permanent until its duration ends. Thus, if you can find a ring enchanted with Chameleon (say, through the Daedric quest for Meridia), you can keep it on for a large bonus to your sneaking abilities.

Bold-Faced Thievery

Sneaking is more or less required to commit most of the crimes available in the game, such as lockpicking, tresspassing, and theft. At heart, if you commit a crime while in Sneak mode, it essentially didn't happen.

For instance, if you're inside someone's home and see a locked chest with a red bag icon, attempting to pick the lock while someone's watching you will ensure that you're met by a guard and hauled off to jail, probably before you're even able to leave the house, regardless of whether you actually took anything out of the chest or not. If, however, you're successfully in Sneak mode (i.e. the icon is grayed out), you'll be able to pick the lock and loot the chest without any ill effects. The same goes for grabbing loose items on tables and shelves.

Thus, masters of Sneaking will have a large number of homes and shops to burglarize and loot, whereas characters that haven't boned up on their Sneaking ability will find themselves getting followed around in shops and homes when they make their presence known to the inhabitants. Low-Sneak characters will also have a harder time creeping around sleeping characters, who are more likely to be awoken by the noise made by a poor Sneaker.