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Pathfinder 1E Tailing Someone

My party is going to be following someone soon. Their goal is to follow the mark to wherever he is going and see what he's up to. How do I make this interesting? I don't want it to be "Ok, roll stealth. ... Alright, he doesn't notice you". The dice do seem to hate me so I try not to put everything on a single roll for my players.

The mark is a goblin who is heading to the old ruins of a lighthouse. There, he's found some magic items he's using to learn to read and write; a taboo for goblins.

I've thought about maybe adding in some other challenges. Like a wild animal begins to stalk the goblin mark and the PCs have to protect him discretely. But that all feels very video game-y.

Thoughts? Advice?

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tailing someone? An interesting take on pin the tail on the donkey perhaps?

But seriously, if its the whole group, this guy should get SERIOUS perception bonuses. Imagine those anime scenes where 6 people hide behind 1 pole. I'd suggest 1 person do the tailing, and use communication magic as the mission progresses.


Last convention we went to had an AL module where we tailed someone through the city as part of the Avernus set. It was ok, but felt like we could not lose since it was part of the plot to not fail. I guess you need to have a chance to fail and repercussions for failing. There could be guards that now suspect the PCs of being sneaky or thugs that work for an organization that is allied with the goblins. Maybe the goblin sees them and leads them to a trap that catches them or hobbles one of them (the way healing works though may make this harder to pull off).


Typically if your being stealthy you go slower. So it become difficult to tail someone that way.
What I would do is point that out to the players and ask them how they want to follow the Goblin.
If they want to be stealthy , the Goblin will probably outdistance them. If they hurry, then stealth checks with penalties.
They could try following his tracks. Or follow him at a distance. Penalties on his perception checks to see them.
But they might lose sight of him etc.
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You can have the goblin meet someone or stop at a place like a tree or rock wall and exchange something. Meeting someone gives the PCs opportunity to persuade/bluff/intimidate, while a secret cache gives other chances to find something. You can hide the drop off with some other text about stopping to tie his shoe or drink some water. Looking around before acting suspiciously could be a clue to the players.

There could be simple traps along the path as well meant to trip or net people following him. "You see the goblin start to hop around randomly before jumping to a large rock along the trail."

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