3 Questions to ask a high-end escort for a Castle Infiltration

[mistermarv]

Hi D&D Gurus,

I am seeking advice regarding 3 questions that I can ask my DM for an upcoming castle infiltration.

Basically, my half elf sorcerer went to a brothel to scout the place and gather information. Being a care free spirit, he decided to mix business and pleasure together and made a friend/contact in the form of a lovely young escort who happens to hears the a lot of information from the patrons who come to this high end brothel. This brothel is visited a lot by many high-end customers, including staff that works in the castle. Because of this my DM has told me that I am allowed to ask 3 questions.

Our mission is to infiltrate this castle and stole a magical artifact.

The background story is that the best friend of the local lord murdered him, overtook the castle and currently reigns in the deceased lord’s castle. The guards have been changed into people loyal to him and he is guarded by 6 elite knights of which 2 of them is currently in the area.

We met the former guard captain of the deceased lord and they will be helping us to infiltrate the palace. The locals dislike at least 1 of the 6 knights a lot.

I guess my question would be: What kind of information does my sorcerer can get/ask from a high-end brothel escort for this castle infiltration mission.

Currently, I am leaning toward the following question:

1. How can I blend as a servant to infiltrate the castle using a disguise?

2. Unsure yet

3. Unsure yet

My sorcerer is proficient in the following skills:

- Arcana

- Deception

- Insight

- Intimidation

- Investigation

- Perception

- Performance

- Persuasion

- Stealth

Spells that I have and might be useful:

- Detect Thought,

- Detect Magic,

- Suggestion


Looking forward for your responses


Kind regards,

[nickl_2000]

-How do the people sneak you in and out without being seen? (I would imagine that an escort would be scandalous in the politics, so there must be a secret/hidden back way that they would be snuck in and out of the castle to avoid attracting attention.

-Are there any servants or castle staff who are not loyal to the new Lord, that would assist you once inside?

-What sort of traps are set up around the castle that the staff needs to avoid to stay safe?

-Are there any guards that have a weakness for a specific food or drink? (something that could be delivered to them with a sleeping drought or poison that they would definitely eat/drink)


That's what I can think of at the moment.

[JeffreyGator]

So the escort has heard from people in the castle but it is unclear if the escort has been in the castle. This is probably going to lead to distraction while you steal the thing or blackmail in order to steal the thing with help.

What shifts in personnel have happened at the castle recently?

How can the castle be best entered discreetly/inconspicuously? (This applies even if the escort has not entered since clients may have needed to stay late / get back early...)


Are there secrets that you can share to get people in the castle to help?


Are there people in the castle still loyal to the old lord and willing to work against the usurper?



You may also need to be careful to avoid questions that she could get you in trouble by telling the guard that you were asking about.

[ErHo]

-How do the people sneak you in and out without being seen? (I would imagine that an escort would be scandalous in the politics, so there must be a secret/hidden back way that they would be snuck in and out of the castle to avoid attracting attention.


Sounds exactly like the story of Rahab the Harlot letting the israelites in at night through her window.

https://missionbibleclass.org/old-testament/part1/conquering-the-land/rahab-helps-the-spies/

[Joe the Rat]

I wasn't sure if it was going to be about a military accompaniment, or a lady of the evening.

I am not disappointed.

You might consider timing. If this isn't time critical, there might be an event conducive to sneaking in - some sort of feast or gathering, or a high-activity time within the castle. It's a risky question, but it's as much an offer to the DM - create an event that provides cover and potential world building or social encounter oportunities.

[Montesquieu P.]

Sigh. First off -- to whom will the lady/escort in question have a greater loyalty? To whom will the brothel's manager? If they get steady, good custom from the castle, why shouldn't they tell you all -- and then rat you out to the guards as soon as you've left?

To make the tangle worse, if you are too indirect, you'll risk a miscommunication that completely bolloxes the situation ("Oh, you meant Castle Greenwood, not Castle Deadwood? Ooops!"; or worse, "Oh, you meant you wanted to kill everyone inside including my cousin, not just the evil usurper?")

...so use the Detect Thoughts and Perception to gauge the intentions and thoughts of the lady/escort as you probe, first, about how willing they might be to help. Don't forget you can always pretend to be a 'Tiger Team' hired by the "good guys" to test the castle's security, if the local is loyal!

Only 3 questions? Then you'd better do a lot of legwork around and outside the castle, and concerning its occupants and patterns, before you query the 'inside source'. Don't use them for otherwise readily-obtainable detail.

Make your questions open-ended; because "How would someone go about getting into the castle, and then the lord's chambers, safely and undetected?" is more likely to garner more useful information than "Is the lord's chamber guarded?"

Suggestion may earn you a very detailed data-dump...at the risk of the spell-recipient knowing, afterwards, that they've been 'pumped'. Got a disguise ready?

Include a question about "Who can you think of who will know more, and be willing to talk with me, about how to get past the guards without raising any problem or causing any harm to anyone?" You've found a source, but the best information they may have to give, is a better source.

A third question should be about the timing -- both of the day, and of the week, when the penetration is easiest accomplished. You may have to plan some extensive 'wait time' within the grounds.

The best assassins aren't unseen, they're just not noticed. Going in, at work, or leaving.