Stealing skill
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The Stealing skill encompasses a wide variety of theft-related skills. These include robbing coins from the pockets of characters (both PC and NPC), shoplifting, and stealing gems from players' open containers. The skill also has a few more esoteric applications, almost all of which are considered game secrets.
The Elanthian justice system understandably treats these acts as criminal offenses. Stealing from NPCs carries the charge of Pickpocketing, and is the lightest of the stealing offenses. More serious charges of are those of Pilfering from shops and "Felony Stealing", which is stealing from another player character.
Teaching
The teaching of stealing was once permitted almost everywhere, but has relatively recently been declared a crime. A mechanical alteration has made it so only guilded Thieves may teach stealing, although the in-character reasoning behind this sudden reality-jolt is dubious at best.
Stealing from shops while hidden will result in the gain of Stalking and Hiding experience.
Guild Interactions
Paladins are not permitted to learn Stealing. They will suffer guild-specific penalties, including loss of soul state and inability to circle, if they somehow learn the skill for any reason. To unlearn any experience that may have been learned, a Paladin needs to go to Chadatru's altar in Theren Keep and REPENT.
Advancement Quirks
Stealing is seldom counted for guilds' survival requirements.
Bonuses
Agility and Discipline boosters will help with stealing. If one has more hiding and stalking than stealing, those skills will provide a small bonus to stealing while hidden; if not then it's best to steal while unhidden. Thieves get bonuses from Urban Bonus and Confidence.
Defending Against Stealing
Until recently, Stealing was also the skill used to determine how difficult a player was to successfully steal from. Perception was used to determine if the would-be victim noticed the attempt. It was conceivable that a character with high Stealing and low Perception would be difficult to steal from but would hardly ever notice an attempt, and that a character with high Perception and low Stealing would be easy to steal from but would almost assuredly catch the thief in the grab. In 2007, this was changed so that Perception would apply to both of these checks. Non-larcenous characters, therefore, now have no reason to need to train Stealing at all.
Many of these measures seem to have been implemented to give Thieves Guild members a larger advantage over other player characters in conducting these sorts of crimes. For a period in the early 2000s, other guilds' abilities were sometimes viewed as more beneficial overall to a life of crime than the Thieves Guild's. This was especially true of Moon Mages, who have many magical abilities that allow them to be stealthy and elusive.