D&D 5E Telepathic Stealth

[Herosmith14]

So I have this idea for a thieves guild in a campaign setting I'm making that would be loosely based on the Psicorps from Babylon 5. It would be composed of mystics, Ghostwise Halflings, GOO warlocks, a few kenkus (for forging physical documentation), and possibly knowledge clerics, though I'm not sure how to incorporate them.

The idea is that Immortals, Wu Jens, and Soul Knives would act as muscle, and Nomads would be thieves. Telepaths would be perfect for collecting blackmail (Awakeneds in particular), and telekinetics make efficient assassins. As with the knowledge clerics, I'm not sure what role Avatars would play in this guild.

I ran into a problem with the blackmail thing, though. The idea was that the telepaths would attempt to search the victims memories without them noticing. I'm struggling with how you would pull that off, would it be a Stealth check? Insight? Investigation? I'm also presuming that the victim would need to roll something to see if they notice if they're being scanned, so would that be Insight, a saving throw, or what?

The purpose of this thread is to try and figure out the Telepathic Stealth thing, and maybe to help me place knowledge clerics and Avatars. Thanks

 

[ClaytonCross]

I would like to point out that the Telepathic ability of Awaken Mind Warlocks is a one way "speaking" ability according to sage advice.

http://dnd.wizards.com/articles/features/sageadvice_july2015

That said, if your DM, Home brew as you want. Perhaps this one group is different for some reason...

It I was looking for a mental challenge I would:

Insight vs Deception <-- For a mental stealth test
--If they fail the stealth, or attempt to pull information without the stealth test, then the target knows and has advantage to prevent from pulling information.

Wisdom vs Wisdom Save <-- For a the test to pull out any information
-- Any failure vs the Wisdom Save, gives the target a cumulative +10 to there Wisdom Save and Insight test against mental search on the same day. As they gain mental resolution to defend against physic attacks for 24 hours (to prevent more than 3 failed attempts on a specific target, since otherwise you would just hand wave they continually try until they succeed or get stuck in dice rolling hell, Kind of like a raising DC for continual failed skill tests)

Just my thought on it anyway.

 

[Herosmith14]

I would like to point out that the Telepathic ability of Awaken Mind Warlocks is a one way "speaking" ability according to sage advice.

http://dnd.wizards.com/articles/features/sageadvice_july2015

That said, if your DM, Home brew as you want. Perhaps this one group is different for some reason...

It I was looking for a mental challenge I would:

Insight vs Deception <-- For a mental stealth test
--If they fail the stealth, or attempt to pull information without the stealth test, then the target knows and has advantage to prevent from pulling information.

Wisdom vs Wisdom Save <-- For a the test to pull out any information
-- Any failure vs the Wisdom Save, gives the target a cumulative +10 to there Wisdom Save and Insight test against mental search on the same day. As they gain mental resolution to defend against physic attacks for 24 hours (to prevent more than 3 failed attempts on a specific target, since otherwise you would just hand wave they continually try until they succeed or get stuck in dice rolling hell, Kind of like a raising DC for continual failed skill tests)

Just my thought on it anyway.

Good idea. I might do Investigation vs Wis save for retrieval, but still thanks!