Oblivion:Sneak

The Sneak skill allows you to move around undetected, pick pockets, and do more damage to targets if you attack while sneaking.

In-game Description: Pick pockets and move unseen and unheard by observers.

Mastery
Mastery Perks
A Novice gains a 4x damage bonus for one-handed weapon and hand-to-hand attacks - and a 2x damage for marksman attacks - when undetected.
An Apprentice gains a 6x damage bonus for one-handed weapon and hand-to-hand attacks - and a 3x damage bonus for marksman attacks - when undetected.
A Journeyman receives no penalty to their chance of detection while sneaking for the weight of their boots.
An Expert receives no penalty to their chance of detection for running while sneaking.
The attack of a Master on an opponent ignores the opponent's armor rating as long as the player is undetected.

Skill Increases
You gain 0.75 experience points every second (real time) spent moving in sneak mode without being detected, but only if there is a person or creature nearby.  No experience is gained when sneaking with nobody nearby or if you are standing still, or from "quest" followers (e.g. Viranus Donton during The Master's Son).  You also gain 2 experience points every time you successfully pickpocket someone (regardless of the value of the item stolen, and even if you don't steal anything).

You will gain Sneak skill more rapidly if you spend most of your time exploring the wilderness and caves in sneak mode.  However, you will move more slowly, and most of the time you will not be gaining any experience (because nobody is nearby); you could instead be gaining Athletics skill during that time.

Sneak can very easily be auto-trained: face a wall (using any of the following tips) and use the auto-run key (PC) or hold the joystick forward (Xbox/PS3).

Tips for increasing Sneak somewhat more artificially include:
Sneak near people who are asleep e.g.,
People sleeping in guild houses of which you are a member.
City/castle barracks that are open to the public are also an option (no locked doors to open - hence one is not trespassing).
Homeless NPCs.
The Skooma Den in Bravil - the inhabitants sleep all night, all at the same time, and it is not trespassing; enter during daytime, wait until night time, and sneak into a corner or bed.
The eternally sleeping prisoner added by the Vile Lair plugin.
Rufio, who can be found sleeping in the basement of the Inn of Ill Omen (if A Knife in the Dark has been started).
The worshippers at the Shrine of Peryite while they are frozen.
In the White Stallion Lodge while Mazoga the Orc is sleeping.
Sneak behind walls that hide you from nearby people or creatures:
Armand Cristophe while he is in the  Garden of Dareloth.
Guardsmen in towns.
Any time you detect a nearby creature in another room using Detect Life, you can keep sneaking and gain experience.
Sneak towards the wall at the very start of the game, before you approach the cell door (and hear Valen Dreth's taunts).
Sneak in Jauffre's room with the door shut in Cloud Ruler Temple. There is a Blade outside 24 hours a day.
Go to The Grey Mare Inn in Chorrol. Walk up to the top of the stairs. Turn around and there will be a ledge. Jump onto the ledge and keep walking into the wall. The innkeeper never moves, so you can sneak there as long as you want.
Go to The King and Queen Tavern in the Elven Gardens District of the Imperial City and go upstairs to sneak behind the door leading to the rooms. None of the NPCs will follow you upstairs and the innkeepers will always be close by.
Go to the Arena and sneak on the top part of the ramp leading to the Bloodworks.
Sneak inside Anga after completing Namira's quest. The denizens can also be rapidly pickpocketed for quick points.
Use Invisibility or Chameleon and sneak around any awake person.
Sneak behind an Imperial City guard on their night patrol. 
Sneak behind someone who is sitting, such as the prison guard in the Bastion. If you're in a forbidden area, keep in mind that the person may eventually get up and notice you.
Your horse counts as a creature to sneak around. Ride to a corner, turn your horse away from the corner, and sneak into the corner. This will allow you to keep walking forward in sneak mode without actually moving and remain close enough to the horse to be considered sneaking.
If you have the Frostcrag Spire Vault, your Vault Guardians are also creatures to sneak around. Stick yourself behind a stack of crates and just auto-walk. The crates are high enough that you can also cast without being seen, so with a magicka-cheap spell, you can train two skills at the same time.
Take a follower with a low Responsibility to a location where there is no one around (e.g. your house) and pickpocket him repeatedly.
On the long Red Ring Road bridge across the Upper Niben at the southeast corner of Lake Rumare is one the guaranteed Khajiit Highwaymen. You can sneak anywhere in the vicinity of this NPC and repeatedly enter and re-enter his inventory without being detected criminally, essentially meaning you cannot be booted from the NPC's inventory for being detected, nor will pick-pocketing him be detected as a crime, due to low Responsibility.

See also:
Increasing Skills: General tips on how to improve your skills semi-naturally
Trainers: Pay for Sneak lessons
 
Skill Books: Books that provide lessons in Sneak
Increasing Attributes: Tips on training skills to improve Agility
Free Skill Boosts: Information on the multiple free Sneak skill boosts available
Magic Items: There are multiple generic items which fortify Sneak.
Unique Items: A list of unique items (excluding artifacts and leveled items such as those received from quests), some of which fortify Sneak.
:Unique items include:
:*The Gray Cowl of Nocturnal fortifies your Sneak skill by 25 points, among other things. However, you will be identified as the Gray Fox if you are spotted while wearing it.
:*Shrouded Armor, which is awarded upon joining the Dark Brotherhood after the quest A Knife in the Dark. Among other enchantments, the armor fortifies Sneak by 8 points, while the hood fortifies Sneak by 2 points.
:*Black Hand Robe is a unique set consisting of a robe and a hood. Among other things the robe fortifies Sneak by 11 points, while the Black Hand Hood fortifies Sneak by 4 points.
:*The Ring of the Gray is a reward for completing The Rosethorn Cache. Among other enchantments, the ring fortifies Sneak by 5 points.
:*The Spectre Ring* is obtainable from Hamlof Red-Tooth at Red Diamond Jewelry. Among other enchantments, the ring fortifies Sneak by 5 points.
:*The Raiment of the Crimson Scar, which looks like the Shrouded Armor but with more powerful enchantments (requires the Vile Lair).
  

Dialogue
When your skill reaches 70 or higher, NPCs will start saying: "You're a sneaky looking sort."

Character Creation
The following races provide initial skill bonuses in Sneak:
Bosmer: +10 bonus
Khajiit: +5 bonus

The following standard classes include Sneak as a major skill:
Acrobat; Agent; Archer; Assassin; Monk; Thief.

Remaining Undetected
When in sneak mode, pay careful attention to the eye in the center of the screen.  If the eye lights up, that means somewhere an NPC or creature knows you're there.  Never steal, pick locks, pick pockets, etc. when the eye is lit!  Reposition yourself so that the eye goes dim and you can do your dirty work in 100% safety.  It's really that simple, no matter how many NPCs are standing around, how bright it is, how close they are, just watch the eye. However, the eye lights up even if an ally, your horse, or your summoned creature sees you.
The amount of light that hits your character does matter, so always try and stay in the shadows (and unequip any equipped torches).
Until you become an Expert, walking will make you easier to detect than standing still, and running will make detecting you even easier.
The weight of your shoes has an effect until you become a Journeyman, so take off those nine pound iron boots if you're going to sneak, as barefoot makes the least noise. You can assign your boots to a hotkey if you want to be able to quickly put them back on.
Actions like picking a lock or picking up items (the heavier the item the more so) increase your chance of being detected.
Invisibility and Chameleon decrease the chances of being seen.  Sneak mode complements these spells by also decreasing the chance that you will be heard.
Invisibility is 100% effective, but prevents you from doing anything other than moving.  The spell is canceled as soon as you attack or use the activate button.
Chameleon allows you to do any actions, but is less than 100% effective.  (The implications of combining multiple Chameleon enchantments to reach 100% effectiveness are discussed at 100% Chameleon).
Some creatures and NPCs detect characters in sneak mode more easily than others. Some high-level creatures like Ogres and Storm Atronachs can be hit from a distance (with arrows or spells) multiple times, and they will just look around.  Other creatures like Xivilai will actively search and probably spot you (even at 95% Chameleon) and engage. NPCs with higher Sneak skills themselves will be better able to detect you.
If an NPC is just standing still, yet their line of sight includes somewhere you'd like to sneak to/steal from, you may be able to bump them out of the way.  Sneak up from behind and run into them just a little bit. You will bump into them and they will slide forward a little bit. Make sure you don't bump them too hard or you may slip in front of them where they can see you.  With practice, you can bump them until their nose is touching a wall - or even better, stuck in a corner.  Et voila! You can now sneak/steal anything in the room with them standing right there and they'll never notice!
Sound is not blocked by walls, or even a dozen feet of solid rock. Regardless of the actual topology and connectivity, as long as the straight-line distance between you and an NPC is less than the detection range, the NPC will hear you just as easily as if the two of you were in the same room with open space between you.

Picking Pockets
If you activate an NPC while in sneak mode, you pickpocket them. This is difficult and generally requires high Sneak to pull off. Success rates are influenced by the target's own Sneak skill, the value of the items, and the number of items taken (making gold much harder to steal, since each coin is "an item", and you can only take them all at once) so you may succeed in taking some items while failing with others. Your attempt can be detected even if you don't steal anything (i.e. just by seeing what the person is carrying).  If you fail, the NPC's disposition to you will drop by either 25 points (if you didn't actually take anything) or half the value of the items stolen. If this brings it below their Aggression, they will become hostile if they are confident enough (with a few rare exceptions, see below). They may also call the guards, although if there are none nearby they will not report the crime unless they have a Responsibility of 100 (in which case you will immediately incur a bounty).
If you are caught pickpocketing by an NPC that objects to the attempt, you will not be able to pickpocket that NPC again until the next day; the reset occurs at midnight.

There are some characters who will not become un-pickpocketable or hostile even if they catch you, and pickpocketing increases your sneak skill fairly rapidly.  You can repeatedly hit the pickpocket key to open and close the inventory screen. You will still incur the 25 point Disposition hit each time though, and still need to be out of sight of any guards. These "safe" pickpocketing targets include:
A Highwayman (after you've let him rob you).
The Adoring Fan.  Tell him to wait, then sneak behind him and start picking his pockets.
Mazoga the Orc.
Gaston Tussaud on his ship when he's sleeping.
Anyone in the Skooma Den (except for Roxanne Brigette)
Claudius Arcadia in the Imperial City Prison.
Armand Christophe in his home on the Waterfront.

Reverse Pickpocketing
Once you have activated an NPC for pickpocketing and you are in their inventory menu, it is possible to reverse pickpocket the NPC: you can give the NPC an item, transferring it from your inventory into the NPC's inventory.  You first need to toggle the inventory so that your inventory is displayed instead of theirs.  Then select the item(s) you wish to give the NPC.  The primary limitation is that this only works for zero weight items.

There are two main applications for this trick:
Killing an NPC with a Poisoned Apple or cursed equipment.
Improving a follower's equipment.

Sneak Attacks
Attacking while unseen increases the weapon damage, depending on your Sneak level.  At Novice level, you receive a 4x multiplier for one-handed melee weapons (including fists) and 2x for ranged weapons; at all higher levels, you receive 6x for one-handed melee weapons and 3x for ranged.
The sneak attack modifier only affects the physical weapon damage, not poisons or enchantments. 
Two-handed weapons do not get the damage bonus for sneak attacks (it will be displayed as a sneak attack with 1x damage). If you like to sneak around and use two-handed weapons, keep a one-handed weapon in reserve and use it whenever you want to stab someone in the back.
Generally, longswords or maces are the best weapons for sneak attacks, both having the highest base damage of one-handed weapons.
Spells do not get any sneak attack bonus.
The sneak attack damage multiplier is based on the weapon that you have equipped at the time damage is done.  Therefore, you can get the maximum 6x sneak attack bonus when firing an arrow at a target if you switch to a melee weapon (or become unarmed) before the arrow strikes.  This is most easily achieved with a short duration Bound Bow spell and firing at the last second.
While in sneak mode it is possible to murder an unsuspecting NPC, even in front of a guard. Of course this is most easily done with a bow.  If you're close enough, you'll hear the guard mumble about how "a murderer is on the loose" and how "the body's still warm". However, as long as you were not seen making the shot, and the shot killed the NPC instantly, you will be exempt from suspicion. If you are spotted taking the shot, quickly take the items and turn yourself in. You will get to keep the items, as they are not considered stolen. If you do not take the items, but turn yourself in, the body may not be there when you come back.

Melee Sneak Attacks
When using a melee weapon or attacking unarmed, sneak attacks continue for as long as the enemy does not have you targeted, meaning multiple sneak attacks are possible. This is easiest if you are directly behind your victim, since they will be briefly stunned by the attack.  If you can quickly attack again before they have a chance to turn around and see you, you will get another sneak attack.  The key to success is speed, so using a fast weapon (such as a dagger) greatly increases your chances.
Only detection matters: even a target that is paralyzed or otherwise "helpless" has no impact on whether you can make multiple sneak attacks or not.

Sneak attacks do not "combine" with power attacks: you will only get the sneak bonus. (Otherwise, you would get an 18x damage modifier, which is enough to kill just about anything in the game instantly.)

Be careful when sneak attacking creatures with Reflect Damage if you are low on health, as the portion you take will also be 4x or 6x normal.

Ranged Sneak Attacks
Multiple strategies can be used to allow multiple sneak attacks when attacking with ranged weapons (i.e., bow and arrow).
Your chance of being detected when hitting an opponent with an arrow while sneaking is based - at least in part - on how far away you are. If you shoot while nearby, the enemy will likely spot you immediately and attack. If you are far away, you may be able to remain hidden. Line of sight is also a factor. If you are partially hidden you can remain undetected longer than if you were out in the open. 
The enemy doesn't start looking for you until hit, so you can take cover and remove yourself completely from the enemy's line of sight right after you release the arrow, while it flies, before hitting the enemy.
When you sneak-hit an enemy with other enemies nearby, their reaction depends upon your distance to the enemy that you hit, not on the distance between you and nearest enemy, so sometimes it is better to try to hit the enemies that are farthest away.
If you are directly behind a target, it is possible that it will not even move after getting hit and will make no attempt to turn around and see you.  If you find such a sweet spot, you can shoot repeatedly and keep getting the sneak bonus over and over until they are dead.
Many monsters and NPCs will run towards the area the shot was fired from even if you stay undetected, so it is usually best to scout out a position you can move to after firing the shot. It is often easiest just to sneak back to where you came from after firing the shot. Having at least two or three shooting locations decided before starting the battle is essential in battles where your success will depend on getting enough stealth attacks in before being noticed.
While a melee sneak attack is slower to deliver than a normal melee attack, shooting arrows from a sneaking position has the same rate of fire as shooting from a normal position.

Playing a Stealthy Character
Playing a stealthy character means fighting smarter, not harder.  Toe-to-toe battles can almost always be avoided.  You never want to be in this situation; thankfully if you play smart, you will rarely be forced to fight a fair fight.  Use all of your surroundings to your advantage.  If your opponent is on or near a wall/ledge, maneuver yourself so your first sneak attack sends them flying over the edge and the fall will kill them.  Goad enemies into chasing you and run up to a guard who will kill them for you.  Traps found in dungeons can also be carefully used to damage enemies.
Night-Eye and Detect Life are very helpful effects for stealth. It's easier to sneak in the dark, so it's imperative to see well yourself and know when something (or someone) is around the corner.
Get these effects from your race/birthsign if you can - you will have them both on constantly.
Being a vampire adds the ''Hunter's Sight'' spell, for a very low cost (5 magicka).
With access to the Arcane University or the appropriate Sigil Stones, you can enchant rings or other items with Night-Eye and Detect Life. You may also find such objects on your adventures.
A useful unique magic item is Fin Gleam, a helmet that gives you constant Night-Eye, Water Breathing, and Detect Life 20 feet on Self.
Hotkey such items, so you can toggle their effects on and off quickly and easily, for instance, to check how well concealed you are in the shadows.
Night-Eye can sometimes be a handicap, as it makes it much harder to spot dark areas and keep out of the enemy's sight.
Detect Life can also be a handicap, because the diffusing glow can make it difficult to see which direction an NPC is facing.
Alchemy is a very useful skill at higher skill levels, especially for stealthy characters. It is possible to make poisons that can deal around 700 damage over a span of 30 seconds or so, or potions that collectively restore amounts of Health, Magicka, and Fatigue near or in the thousands.
Use enchanted/poisoned weapons as appropriate:  
Acquire/enchant a weapon with Silence for use against spell casters.  They go down fast when they can't summon or heal themselves. 
Acquire a weapon with Paralyze (if possible; this may be easier said than done) for NPCs and creatures with a lot of health and offensive power. 
For a very effective sniping bow, place Drain Health 100 (1 second) on a bow in addition to normal damage effects. This works equally well with a melee weapon. 
If you get into a pinch, do not be afraid to use any poisons you might have. You can use one per swing if need be, and this can easily be the deciding factor in the outcome of an otherwise-fatal battle.
It may be worth taking a look at the Useful Enchantments page as well, for more ideas for equipping a stealth character.
The best weapons for sneak characters are the kind that kill instantly (1 sneak hit = 1 kill).  At higher levels it is very hard to create or find such weapons (draining health is the best enchantment, combined with the sneak attack damage bonuses), especially against tough creatures and warriors. High damage spells from afar are also great.
The third-person view is extremely helpful, allowing you to look around corners and see which way your enemy is facing, what kind of equipment they have, and exactly where they are.

Messages
The following table provides the messages that are displayed when your Sneak skill levels up.



Notes
Once your combined Fame and Infamy reaches 10, you can visit the Jone Heaven Stone to receive the greater power ''Jone's Shadow''.  One of several benefits of this power is that it fortifies your Sneak skill 30 points once a day for 120 seconds.

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