D&D 5E DMing Question: Framing my PC's infiltration into secret organization

[Ancalagon]

One thing to consider is what capacity does the V.A. have to "screen" potential agents, and how circumspect have the PCs been so far? Your group may be the exception, but most adventuring groups are brash, loud and stick out like sore thumbs. That makes them really poorly suited for infiltrating a secret society like this. Sneaking in at night and smashing the place yes, but that's black-op, not long term deception/infiltration.

(There is also the reality that there are probably 1-2 PCs that would be pretty good at this, but the rest is mediocre/horrible. And some of the players won't have the skill or interest for it. So what are those PCs and players supposed to do? Sit tight for an entire session?)

So unless the V.A. is unusually trusting, has limited divination magic capacity AND your group has been operating in a circumspect matter *all the time*, the V.A. will almost certainly find out who the PCs are. At this point, I think that the V.A. will wonder "why the heck do these guys want to talk to us?!" and start digging further.

The V.A. could just walk away and break contact, but that's no fun. I think a more fun thing is for the V.A. to use/test the PCs while they investigate in the back. Several good suggestions were listed above.

 

[darkbard]

Good points, all, Ancalagon! This is the initial framework for our new game, following an assassination attempt in which the PCs intervene to open play, and the PCs are first level: one just arriving in the city of Tyr from the Wastelands (Druid), one a halfling expelled from his tribe and masquerading as a street urchin (Rogue), and one a recently-freed slave gladiator (Fighter). So, as such, they haven't (yet?) established any reputation for themselves.

One thing the various setting books suggest is that the VA is always on the lookout for Preservers (read: any practioners of magic that do not defile the land) to protect from persecution and potentially to enlist them--and their allies--in the fight against oppression and the evil workings of Defilers.

Nevertheless, you're absolutely correct in suggesting there should be some impetus to and mechanism for the VA to vett the PCs' backgrounds (as well as their current motives and actions, which will involve actual gameplay) to the extent of their abilities!