How would you scout a party, you need to kill?

[HoboKnight]

Hey,

so, my party got targeted by an assassin brothers, (2 of these guys: https://www.dndunleashed.com/home/new-monster-oni-nightblade) who want to a) survive b) get the job done.

They have a vast amount of money at their disposal and want to do initial scouting on the party. Since they are experienced assassins, they will also do legit scouting, before they move in for the kill.

How would you go about this? I see this thread as a question-and-answer - you guys saying, what would you do, me providing answers, assassins would get due to their enquiry. This way I can roleplay these guys in a proper way.


Let's do this :)

[JackPhoenix]

The most important question is how game-as-war or game-as-sport you want to go. The latter means coming up with some limitations, because you'll want the fight to be a fair encounter. The former, you can go as dirty as you want, which may not be fun for the players. The optimal moment to strike, after all, is when a character is away from the rest of the party, unprepared for a fight and vulnerable.

Do the assassins have time schedule to maintain, or can they take their time? How much do they already know about the party and their capabilities? What's the setting? The available options and optimal approach are different if the characters stay in a big city or if they are constantly on the move.

In general, Change Shape means they can assume inconspicous forms and get informations simply by talking to people that know the characters (Charm Person may help there), or even the characters themselves. They can pose as helpful NPCs, perhaps even killing and replacing existing NPCs to get closer to the characters. If the party lacks means to see through the deception (how big, what level and what characters are in the party, anyway?), they can start indirectly... sell them cursed items, poison their dinner (midnight tears poison is pretty great for that, because it doesn't trigger immediately), give them bad informations leading to a trap, hire other mercenaries, then jump them when they are wounded and exhausted.

[HoboKnight]

O, hey, helpful man :) We meet again. :D

So: This should be skewed rather toward game-as-war.

Assasins can take their time. Party has been scryed upon by the guy who hired assassins. Sadly, he never managed to scry them during a combat. He knows their names and that the party consists of:
- skinny elf with a greataxe
-dwarf in a fullplate, with a shield and a hammet
- dragonborn in full plate with a greataxe
-elf in full plate with hily symbol
-human in a full plate with no obvious weapons

Setting is 5e Feywild. Party is constantly on the move, currently in a major trading hub(city).

Party level is unknown. How would one assess that?

How do you talk to party inconspiciously? Ask them for help in a minor quest to see their abilities?

ATM party location is difficult to pinpoint, because Scry is not 24/7 and party migrates a lot.

Actually approaching PCs to help the assassins, is a good idea. First run PCs do, asssassins see their power level. Second dungeon, they wait for party to have resources drained, then they move in for the kill.

.

[JackPhoenix]

The Oni have decent Arcana bonus, so it's reasonable to assume they know plenty about magic. If they can see what spells the party casts, they can get rough idea of how powerful they may be. That does not necessarily mean they'll have all the information... they simply may not have seen their most powerful spells, but it provides an assessment of a minimal level: If they see a 6th level spell, they know the party is at least level 11, and can make guess what other magic may be at their disposal. Getting someone/thing else to start trouble for the party to deal with is also an option. Detect Magic... even in a shapechanged form, like random person in a marketplace or a tavern... may help in figuring out what magic item the party has at their disposal.

They may hire the party to assess their capabilities, or maybe the party enjoys time in a tavern when "some other adventurers" start a bragging contest about their exploits, and invite party to share their stories. You may buy them few (non-poisoned, for now) beers to make things easier. Again, it's not reliable... the party may not tell everything, and they may embellish things, but it's at least something.

Now, if the party moves along a lot, it complicates things, but at-will Invisibility and decent Stealth bonus may make shadowing them easier.

Try to find out their individual weaknesses and flaws... if one character is a womanizer, or likes to get drunk, that's an option to lure them away from the party and make them vulnerable. Ideally, the assassins should avoid circumstances when they have to fight the entire party, even weakened... attack when they are sleeping alone in their rooms. Attack them when they are bathing. Don't be afraid to run the moment things turn against you (if you can grab a magic item before you Shadow Jaunt away, all the better!), but remember, the party now knows you exist, and depending on their capabilities, may deploy divinations to find you... if you can get your hands on an Amulet of Proof against Detection and Location or a Ring of Mind Shielding, do so. If you can use the shapechanging to mislead them to shift the blame to someone else, all the better! You have time, you may wait for the right opportunity. Patience is a virtue for an assassin.

Speaking of Shadow Jaunt, consider having some other creatures around when you attack so you can use them as a target for the teleport. It doesn't need to be anything fancy... charmed commoners or random small animals are valid targets.

Make sure they stay down. Yes, conventional wisdom say you should geek the mage, but healers (once identified) are more important. After all, you don't want all your hard work to be undone by a Healing Word or pesky resurrection magic. Finish off the fallen. Even if you attack the whole party, you don't need to finish the job right away... kill one and run. Steal or mutilate the corpses (beheading means no Revivify or Raise Dead, stolen (but not destroyed) corpse means nothing works).

[animorte]

Plant some heat metal scrolls or traps and diminish the returns from all that plate armor, then move in, haha. Or some magnets, ruin just about everybody’s day. Unfortunately that would require them to have some idea of where the PCs are headed next, which seems to be one of the issues.

[Selion]

It depends if it's a urban setting or if your players are currently in the wilderness.

I think the most safe way would be ambushing the party in a town (unless they are in a metropolis with magic-countermeasures). In the crowd, using their shapeshifting abilities, they hardly will be noticed, shapeshifting is safer than invisibility, because it's not revealed by see invisibility or true sight. First your Oni-es need to observe the party from distance, understanding their habits.

I will approach them either personally or trough a charmed villager, findong an excuse to divide them, eventually ambushing a lone player in 2 vs 1, chipping away the remaining PCs one at time.
Remember they have gaseus form at their disposal, so if they can lure a lone PC in a room, they could easily enter trough the keyhole or other small fissures.

If the party members always stick together, a common way to take them unprepared is attacking them during their sleep, your players are likely to have been developed a safe resting routine by now, using Leomund tiny huts (which note well is a HEMIshpere, so if, for example, they use this spell in a room with wooden floor, it's possible there is a little hole to infiltrate inside the sphere) or being hosted by allied NPC (I don't know your setting), so it's possible for this strategy to fail.

In the wilderness it's not so easy, one of the oni could pose as a traveler in search for help and eventually join the party for a brief period.


BTW
I had a similar situation with a Rakshasa in a game in which i was the DM (system pathfinder). I used disguise self and suggestion two times, the first to create havoc in a crowded place, using a villager as a pawn to assault a random civilian, then the rakshasa, posing as a guard, called one of the players for help (the most loyal and helpful one in the group), using again suggestion to make their request more plausible, ambushing him one on one in a alley.
The PC survived, because of bad rolls on the demon cat part, after a few rounds of combat the rest of the party came for help, and they disposed of the evil foe. The look of terror in my player's face when he understood what was happening has been priceless.

[Demonslayer666]

I would have the assassins hire someone to join the party and report back with a sending stone.

Investigate the party's past accomplishments. Divination magic would also help.

Possibly hire someone to attack them.

[greenstone]

A novice adventurer approaches the PCs in a social setting, gushes about how much they admire the PCs, and wonders sheepishly if he could join them in a drink or two and ask a few questions, drinks on him or her, of course.

A few drinks turns into a few days as the fan follows the PCs around, flattering them. Perhaps the fan turns into a follower, a hireling, accompanying the PCs on adventures.

And all the while observing them closely.

[Throne12]

First off Surprise assassinations is a no go area for DM's. From a players pov it's equivalent to ( Rocks fall you all die). So if you got good players that don't meta game I would do what I call Cut scenes. Narrate a scene where there are two shady figures paying a wizard to cast a scrying spell. If it's in a city/town the party been in for a bit they might know people. So someone they know might tell the party ( hey there were some shady guys asking about yall).

My point is that you got to let your players know something is happening. This will keep your player feeling like it was a hopeless Situation that you put them in and it builds up Suspense. So if your players are not meta gamers I would use cut scenes if they are or you don't want to chance it drop Obvious hints with 1 or 2 Red herring's. Other then that go crazy on how your assassins gather and prep. Oh I also for got give a clue or 2 for everytime your assassins gather info or do any prep.

[Selion]

First off Surprise assassinations is a no go area for DM's. From a players pov it's equivalent to ( Rocks fall you all die). So if you got good players that don't meta game I would do what I call Cut scenes. Narrate a scene where there are two shady figures paying a wizard to cast a scrying spell. If it's in a city/town the party been in for a bit they might know people. So someone they know might tell the party ( hey there were some shady guys asking about yall).

My point is that you got to let your players know something is happening. This will keep your player feeling like it was a hopeless Situation that you put them in and it builds up Suspense. So if your players are not meta gamers I would use cut scenes if they are or you don't want to chance it drop Obvious hints with 1 or 2 Red herring's. Other then that go crazy on how your assassins gather and prep. Oh I also for got give a clue or 2 for everytime your assassins gather info or do any prep.

These monsters are CR12, i expect this is a long running campaign, players should know their **** (especially spellcasters, it's their job), IMHO this is the point in which a intrigue focused campaign shift from hack and slash to a chess game, that's why high levels are not easy to play, and that's why high level utility spells are so strong.
I agree with you in not ambushing them suddenly out of the blue, it's more engaging creating a build up to this encounter, maybe a villager has seen the oni true form shapeshifting before gathering information on the party.
Btw a high level cautious party is not so easily caught unprepared

[HoboKnight]

Splendid input everyone, really appreciated. Let me just answer a few points:

Throne12
Yes, this is a long running campaign. Party has been Scryed upon for session upon session now. They even had a helpful prophecy for them... but they are sort of very lemming-y.(ingnoring Wisdom saves, ignoring prophecy) They were even hit by a group of not-so-competent assassins already. They killed all of the attackers, took exactly 0 prisoners(were even concidering it for a moment, but nah, let's not be too constructive). They are also aware, creatures can disguise themselves in this setting, but (gasp) they do nothing about it. So yeah, not really "rocks fall" scenario.

I love the patience approach and will use it to the best of my abilities.

thanks, guys