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Message: <blockquote data-quote="Kordeth" data-source="post: 4091614" data-attributes="member: 5036">I think you're overlooking a level of abstraction here. The player doesn't say "I run down Murderer's Alley to elude the guards! I roll a Streetwise check to find a way out!" to which the DM responds based on either of your posited models.Instead, the player says "I want to try ducking down an alley and losing the guards, maybe by squeezing through a gap in a fence or diving down a sewer. My Streetwise result is 24." To which the DM responds "Well, there's no such escape route down Murderer's Alley, so you don't want to go down there--but there is a sewer grate in the alley between the tinker's shop and the tailor's. You dash into the alley, wrench the grate free, and drop into the tunnel seconds before the guards catch up."</blockquote>