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Message: <blockquote data-quote="Arkhandus" data-source="post: 3444340" data-attributes="member: 13966">Bayonet:You've got a point there.  If the pickpocket is successful, he or she is going to get the attention of either local authorities (after the first few days) or the local thieves' guild or something, and will probably have to try something to avoid getting caught by them, after spending an extended period working the area rather than just a brief filching spree.Aust:A good suggestion there, too.Celebrim:But your ideas of handling it, Celebrim, basically neuter and punish the player and his or her PC, rather than accomplishing any greater feel of realism or enjoyment of the game.  -_-I don't mean to be rude, but I do have to point out the flaw in your reasoning; it's way too complicated and makes it difficult for the PC to do just a little something on the side, between adventures, likely at the cost of actual adventuring prowess.  He shouldn't have to invest in a Profession (pick-pocket) skill or other stuff, just to do something he already does well (through putting several ranks into Sleight of Hand), for example.The PHB doesn't have rules for pick-pocketing over a long stretch of time because that's not normally what an adventuring rogue does; he or she is more likely to do a bit of pick-pocketing when it's convenient, or when he/she needs to filch some important item off of an NPC.  Thus it's not covered; otherwise the skill descriptions might include mention of synergies with Sleight of Hand for Appraise, Profession, Spot, and so on and so forth, if the designers' intent was to represent using the skills outside of the normal adventuring manner.It's entirely up the DM's purview to apply synergies and such where he or she feels they are appropriate, but that does not mean a PC Rogue should have to spent 75% of his or her skill points just on being a decent pick-pocket on the few occasions he might be in town between adventures and want to make some dishonest coin.By your description of how it would be handled, it implies that you would expect a PC Rogue to use every skill point at his/her disposal just to sneak past some guards at night and do a bit of spying, and basically be capable of no other skills except those pertaining to sneaking and basic spying.  You'd expect them to make Spot checks, Listen checks, Sense Motive checks, Bluff checks, Hide checks, Move Silently checks, Search checks, and Disguise checks just to get to their spying position without being found suspicious and thrown into jail, not to mention any Climb, Jump, Balance, Escape Artist, Swim, or Tumble checks they might need just to reach the location they'll be spying from.It seems like you'd expect the Rogue to focus his entire skillset (or the vast majority of it) just on one very narrow task.  Not at all fair to the player, or the rest of the group if they have to sit through a few hours of you grilling the Rogue player on what exactly he does to find out what he should spy on, where he should do that from, how to get there, and then exactly how he gets past every guard, passerby, and easily-frightened alleycat along the way, then how he exactly he gets the information he needs and who he decides to spy on, and everything.....This is the impression you give with what you're suggesting.  That an overly complicated and extensive, time-consuming amount of effort go into handling one single task or instance of a task.  And that the Rogue's player should have to suck at almost everything else just so he can be decent or successful at this one kind of task that comes up only occasionally.The skills in the Player's Handbook should already cover their niches individually, with little need to make a big affair of each skill's use by making it require half a dozen others.  Sleight of Hand already represents the necessary skills of a pick-pocket or stage magician, at least when it comes to performing most acts of legerdemain and quick hands.  Other skills can help a bit, but should not be considered necessary for successful and profitable pick-pocketing.  Anyone with decent ranks in the skill should be assumed to have learned the signs of someone who probably doesn't carry money on them (or not much), or someone who likely has a fat purse and is too happy-go-lucky to pay much attention to it, etc.</blockquote>

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