Trailing
Trailing resembles tracking, except tracking is associated chiefly with the wilderness, and trailing typically is used in major urban centers (i.e., cities and large towns). It is the talent of tailing someone—of keeping a certain distance or even catching up to them, though they may be attempting to blend into a crowd, or at least get lost in the confusion of a street full of people.
A proficiency check is first made to see if the thief is able to trail without being noticed. If the person followed has the alertness proficiency, then the thief suffers a -5 penalty.
If the thief is noticed, the person being followed may attempt to evade. To keep from losing the trail, the thief must make another proficiency check. A modifier from -3 to +3 (varying from first time in a foreign city to the thief's home neighborhood) may be used, if the DM so chooses, to reflect how well the thief knows the area. Warn the player beforehand if you will apply modifiers (though you needn't tell exactly what they are).
The DM should feel free to use situational modifiers on these rolls. For example, if a street is relatively clear, the thief should get -1 or -2 on an attempt to follow unnoticed, but +1 or +2 if he has been seen and is chasing after his subject. The opposite numbers could be used for exceptionally crowded situations, or at night.
For any Trailing proficiency roll, a -3 penalty applies if the person followed has the Trailing proficiency as well (and, presumably, knows better how to foil the tricks of his own trade).
Example: Julina is trailing an NPC through the Imperial capital, because she suspects that he is spying for a rival employer and has information that would be valuable for her. It is nighttime, on a nearly deserted street. The DM informs Julina of this, and says that she'll have trouble going unnoticed (-2 modifier on her first roll, he rules, but does not tell her but if her quarry does spot her, he'll be easier to chase (+2). The DM also decides that Julina has been in the capital on this job long enough that she's fairly familiar with the streets and alleys, so she will not suffer a penalty on that account. However, unbeknownst to Julina, the spy she follows has both alertness (-5 modifier) and trailing proficiencies (-3 modifier). This means that her first roll has an adjustment of -10; if it fails, the second will have an adjustment of -6. Julina's Dexterity is 17. She needs to roll 7 or lower on her first roll, but gets a 13 and fails. "The man has spotted you," says the Dungeon Master. "He speeds up and ducks around a corner, into an alley." Julina follows; to keep from losing him, she needs to get an 11 or lower. She rolls an 11, just barely making it. "The alley is empty—you are about to rush through to the next street, but through a window you spot a flash of red, like the man's coat, and hear footsteps up a staircase in the building to your right." says the Dungeon Master. "He speeds up and ducks around a corner, into an alley." Julina follows; to keep from losing him, she needs to get an 11 or lower. She rolls an 11, just barely making it. "The alley is empty—you are about to rush through to the next street, but through a window you spot a flash of red, like the man's coat, and hear footsteps up a staircase in the building to your right."
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