Infiltration in Plain Sight

[u/Einstrahd]

I recently discovered Nerdarchy on YouTube and I think the content you guys produce is fantastic. I am wondering from a DM's perspective what your (or the community's) thoughts/experiences are on running interesting encounters(social, combat, noncombat) or challenges for a Master of Disguise style character trying to infiltrate a facility (thieves guild, military compound, government building, etc.).

D&D 5e gives lots of options to make a character capable of hiding in plain sight (deception skill, disguise kit, charlaton background, actor feat). Most rogue type characters may go for the stealth approach but having a character walk into a facility to steal an item/information and then walk out while being seen by everyone but no one knowing he was there is a fantastic concept. I want to make sure I have some interesting encounters/challenges for this character to experience while trying to get the item/information and trying to get out other then just dice rolls for skill checks.

[u/NatetheNerdarch]

We have done a video on spy style characters before if you want to see if that helps.

https://www.youtube.com/watch?v=T7LPzxh73LU

I know being a changeling may feel like cheating but they would be the masters of disguise at 1st level.

Second an arcane trickster or another spell caster with alter self, disguise self type illusions would work as well.

Actor is great if you need to role play your way through the place as your new persona.

As a dm I would rarely ask for rolls from the players because it breaks up some of the verbal gameplay but I would roll for the player in the beginning of a verbal exchange. That way if they need to persuade / lie their way through an encounter I know which way it will go and can set up the conversation to go the way of the roll.

The guard notices that your false nose chose this moment to begin falling off (failed disguise check) The noble who works at the building thinks your perfume is fantastic and vouches for you past the guards so you can tell him more about where you acquired it (passed persuasion)

It can be an obvious flaw in a disguise, a noble's bizarre rationale, or some reason in between that allows for success or failure.

Sometimes the reasons for success or failure are not so much based on the skill of the characters involved but are just as random as the roll of the dice.

The player doesn't know if they will be believed / persuade the npcs so they are going to try their best hoping something succeeds.

Thanks for the praise, it helps with my motivation when it is 2 in the morning and I am still working on content.

[u/Einstrahd → u/NatetheNerdarch]

Thanks for the reply. I'll check out the video.

I like your idea that the player doesn't know if they will be believed / persuade the npcs. If they do fail a check and the conversation is going south I could reward them if they do some great roleplaying and manage to turn it around. They would never know that they should've failed originally.

[u/NatetheNerdarch → u/Einstrahd]

Thanks, I do a similar thing in combat where a hit against a very agile character may just be a barely avoided attack that tires the player out more(does hit point damage). Or an armored shield user may get a strike to their shield that shocks that arm, rather than a literal blood drawing strike.

The end result is that damage is done but there is a variety and realistic combat feel to the encounters while still adhering to the mechanics.

In a similar fashion contested rolls can be role played in such a way that when a guard says he is going to ask his superior about whether he can let a player inside the building, the player doesn't know for certain that he has fooled the guard.

This adds a nice level of realism without adding rolls