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).
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