The PCs are required to insinuate themselves into a society or an organization for the purpose of spying, stealing something, or inciting a revolt. Infiltration of some societies or organizations may require the PCs to disguise themselves as members of another gender or race (see Disguise below). An infiltration challenge should last at least one day or one week per level of complexity, but it can last for years, if need be.
If the purpose of the challenge is to start a revolt, this challenge should be run concurrently with the Mutiny or Coup challenge. If the purpose of the challenge is to steal something, this challenge should be run concurrently with the Burglary challenge. If the purpose of this challenge is to spy on the society or organization, This challenge can be run concurrently with some kind of social skill challenge to extract the desired information.
Level: PC Level +0 (or as needed)
Complexity: 5 (requires 12 successes before 3 failures).
Primary Skills: Bluff, Diplomacy, Insight, Intimidate, Streetwise, Thievery.
Appearance: The PCs dress in a way indicative of members of the society or organization, making it easier to walk among them. This is good for a single success during this skill challenge. If the infiltration requires disguises for the PCs, this option for success is replaced by the disguises. Unless the group being infiltrated is known for a style of dress, the PCs must first succeed at a Streetwise check to learn how to dress.
Bluff (Moderate DC): The PC actively tries to pass as a member of the organization or society. A Bluff check can be used to fake your way through oaths you are expected to know, secret handshakes, etc. A failed check can result in the PC being disciplined for getting it wrong (often with a lashing or by forcing the PC to perform physically demanding or menial tasks for several hours), or attracting the attention of a doubter. This is good for a maximum of one success per character.
Bluff (Moderate DC): The PC attempts to fast-talk his way out of a failed Bluff. A successful check removes one failure accrued from a failed Bluff check. Each PC is able to remove one Bluff failure in this manner.
Diplomacy (Moderate DC): The PC attempts to keep a low profile, blending in to the organization or society instead of attracting attention. Each PC is able to get one success from making Diplomacy checks.
Diplomacy (Moderate DC): The PC attempts to smooth over a social faux pas made while attempting to fit in. A successful check removes one failure accrued from a failed Diplomacy check. Each PC is able to remove one Diplomacy failure in this manner.
Diplomacy & Bluff: This challenge relies heavily on the Diplomacy and Bluff skills. The party may need to make extensive use of Aid Another to get through the challenge.
Disguise: If the PCs are required to disguise themselves as members of another gender or race to participate in the infiltration, only one Bluff check (at a moderate DC) is required for each disguise. Each successful disguise adds a success to the challenge. A failed Bluff check will result in the disguise coming undone, in a meaningful way, at some point during the infiltration (this is at the DM's discretion).
Doubter: The PC's failure to to Bluff his way through handshakes or oaths has made someone in the society or organization suspicious or doubtful of them. A doubter will watch the PCs very carefully, imposing a -2 penalty to any Stealth or Thievery checks they attempt. If the PCs are successful at the challenge despite the presence of a doubter, he may target the PCs for revenge.
Insight (Moderate DC): The PC spots those who are new members of the organization, or are otherwise easier for the PCs to blend in with. A successful check grants a +2 bonus to the next three Diplomacy and Bluff checks in the challenge. This check may only be used once during the challenge.
Intimidate (Moderate DC): The PC menaces the doubter convincing him to back off. The doubter will not be dissuaded by intimidation, but he will make himself scare for a time. This check removes the doubter's presence for the next three checks.
Streetwise (Moderate DC): The PC gathers information about the society or organization they are going to infiltrate. This skill grants no successes to the challenge, but a successful check gives the PCs reliable information they can use to affect their appearance, or that grants each PC a +2 bonus to their next Bluff or Diplomacy check.
Thievery (Moderate DC): The PC doses the doubter with something that makes him terribly ill but won't kill him. This check removes the doubter's presence for the next three checks.