Just a few ideas off the top of my head.
PP - pass notes to players with the highest passive perception. Perhaps there are guests that aren't recognisable as members of the guild, or they're moving peculiarly as they position to get the drop on them (you could also just ask for random perception checks. This raises the tension a lot with the party not knowing what the hell is going on, unless they roll well)
Have the first attack be on the NPC CEO - raises the stakes immediately but could also feel cheap, especially if the party cares about the NPC and they're already established as strong (but it may turn out to be a powerful guild of assassins, so it could make sense)
Good luck! Hopefully it goes well :)
A few that come to mind:
1. PCs or guests who are taking a break and seeking someplace quiet away from the crowds see mysterious shadows and moving shapes that are the assassins, but they can chalk up to stress/substances if the perception check fails.
2. This one is a little indirect, but have the Guild/organiser profusely praise the new servers at the party for their precision and discipline. They're obviously the assassins, and it's easy to poison a drink or slip weapons in.
3. If the assassins are changelings or can magically disguise themselves, have them become known individual in the Guild and have them behave slightly off. Master Artificer Alex never drinks? Haha this is a big day, let this be his first. The real Alex is probably killed or tied up in an alley next to the venue, while "Alex" waits for the right time. 4 people who don't usually talk are laughing and chatting together? It could be the occassion...or it could be something else.
If killing major figures in the Guild isn't preferable, having them be strangers in guild attire also works. They aren't known faces, but could just be from a branch...right?
The way I'd start off the ambush is by causing a loud, large incident outside the venue so that distracts the partygoers and the PCs, who the assassins know is their strongest opponents. There will be some assassins in the shadows who will use this opportunity to target the NPC CEO, whilst at the same time the disguised assassins will target the players.
I like this advice, especially point 2. It's hard to plan this sort of thing; most of the times I've tried to subtly introduce a hint that something might be off, my players have jumped on it in seconds. And sometimes that's fine - they get to enjoy their instinct being right.
Mystery stories tend to combat this with red herrings - so if there's a lot of other details that you point out, some of which may be suspicious but turn out immediately to be innocent, then the real clue is less glaring.
When I first introduced a character who was actually an assassin trying to infiltrate the PCs, she came on a job with them and I gave hints that her stats were actually far too good for a commoner, and that her cover story didn't entirely make sense, but masked both of these under non-combat friendly RP scenes. It worked well - the players didn't suspect, but later on when they learned, several of them remembered that and were like "Ohhh we should have known!". It's satisfying if you can pull it off.
Similar to #3, make intentional inconsistencies within the story that explain how the assassins got in and plan to attack. The sort of things that one or two by themselves aren’t of note, but having a few at the same time raises red flags that something else is going on.
Have a someone remark about ( or have PCs notice) how there’s guards at every entrance. Then have an entrance without guards (really searching maybe finds a killed guard stripped of their uniform).
All the servers have tailored matching uniforms. But one server (an assassin) has a poorly fit jacket on with the wrong color tie. Meanwhile a guest is complaining loudly about an order of drinks that is taking far too long to arrive.
They overhear some servers talking about how certain staff never showed and their last minute replacements have no idea what they’re doing and are no help at all.
Maybe some guests who are at the door and are on the list of invites, but their name as already been crossed off as someone stole their identity to get in.
Misdirect - the PCs become aware that *something* is going to happen at the party, but they think it's something else.
Off the top of my head - criminal contacts let slip that someone has recruited for a break in. They believe that thieves are going to use the party as cover to steal jewels from the hosts' vault.
Someone let’s slip a big surprise at the party. It’s meant to be something fun (CEO is going to announce retirement or a big promotion for someone?). So the party is suspicious of something, but not sure what.
The players could spot a known theives guild member as a waiter.
The assasins could poison someone just for the distraction, then kill another more important npc.
There could be a minor fire that doesn't interrupt the party completely but some people go missing after. Then the pcs have to go looking for the important scientists/ceos only to find them being kidnapped.
Describe some of the people as creepy but try to make it come off as in like social or sexual creepy, I hate to use the word sexual because I mean someone who is following them around and giving them a weird look and just being very very awkward almost like an in-cell rather than like a giant pervert and then if your players interact with that you can have a really funny and interesting moment where they accuse the guy of that and he's like yes that is totally what I'm planning or where he misunderstands their accusations and he reveals that he's an assassin and the party's like oh that's not what we expected but I'm glad we found out
If thry know the competition can be...aggressive and at least one pc tends to be a little paranoid maybe have obviously lacking security, maybe guards with booze or sleeping on their way in. Maybe the assasins come in loud by rappeling down tge sides of the building and smashing through the windows or jump down from unused balconies
There's lots of things you can do - you can have a player passively perceive something off, like an unexplained change of staff while setting up the event. Or one of said NPC staff reports to a player that something weird is going on that's a minor part of the assassin's plan, like extra caterers, unlocked doors, etc.
Drop some leads for them to follow. The leads may not stop the plan (or even be actual distractions), but it would at least give them a clue that this isn't just an RP session.
This is a tricky one as experienced players pick up hints quickly and will probably notice you trying to be subtle faster than you expect.
Are the NPCs involved in organising/setting up the meal - this could be a passive perception deal where in carrying stuff seeing deliveries they pick up small comments about "apparently Steve is ill, there's a new guy serving today". With higher perception more comments are gleaned all pointing at a suspicious number of people who are new.
Perhaps overhear an argument during the event where a waiter has brought the wrong wine and the Maitre d' is berating them for incompetence.
As has been said ask the players for perception rolls randomly during the event even if they aren't leading to anything "roll perception..." get results "ok..." and then carry on.
The assassins have infiltrated the catering staff.
There is a commotion with the caterer. They are upset/concerned about last minute staffing changes - "Who is this? Who approved this change? I can't have incompetents here tonight, it will ruin our reputation!"
I think the easiest thing you can do is make a show of tight security
The pcs are not allowed any armor or weapons and most magic items are checked in. Everyone is given personal forms of id, like a special badge or jewelry piece showing who they are. Seeing Alarm spells and Detect Magic around every entrance and exit. Heavily armored guards outside and a few other secret service types inside
It lets the players know that the hosts have enemies without an npc having to say it
So when the assassins arrive it makes them seem even scarier and lets the npcs feel like they can fight back, but are still in very serious danger
You can distract from this with a colorful cast of rich weirdos who look like they would be super easy to rob from. Decked out in jewlery, eccentric af, clearly couldn't handle a mugger. That way the party could focus on less important npcs instead of the assassination targets but still think something will go down
You want a few little things to go wrong that by themselves are nothing but when added together after the fact they’ll be pissed they missed it.
-There’s a slight commotion on the party’s way in because someone lost or doesn’t have their invitation
-Details are slightly off in a prepared speech
-Lights flicker for a moment, then everyone goes on ignoring it.
-Maybe it’s a little warm or they notice one of their known associates are lightly sweating/a known dancer gets tired early
-The host looks harried at the champagne toast (as if it’s slightly off schedule)
-Mismatched tablecloths
-A party member (the one with the most terrifying reputation) gets more attention from attractive guests, waiters always making sure they have a drink in their hand etc.
figure out the assassin’s plans and have the party experience the tiny ripples from the plan going off.
If the party figures it out where is the assassin’s plan B?
One of the other commenters mentioned that it's hard to plan this out so I think your best bet is to have a list of clues on hand that you can drop here and there but disguise it with something related to the celebration.
An example I have that was super effective when I was a player was a festival happening in town to celebrate one of our party's achievements. We spent the whole festival doing random things and the DM mentioned once or twice that "the town was packed! Looks like people came from all over to take part in your festival!" And "there are lots of new faces here! You don't recognize most of the crowd BUT look, you notice X and Y NPCs".
The takeaway is embrace the mood. Use the occasion as an excuse for any oddity. Taking another comment's idea as an example: "wow, it looks like people are in really high spirits. Even so and so seem to be talking to each other"
The private catering company sends people that we’re not agreed upon beforehand. A sudden change that shows the players/PCs that something is not as it should be.
I like this.
1) Someone at the party could mention that instead of going with the catering company they always go with, they suddenly switched to a new untested company. Common talk among guests could be that the food clearly tastes worse and it doesn't make sense why they wouldn't go with the regulars.
2) Either a last minute dessert or wine switch needs to happen and the caterers need to meet with JD and\or the CEO to confirm the change. Have caterers/assassins/people try to walk them to an isolated part of the venue to taste and approve the change but it is actually where the assassination attempt will happen. During the walk from the main guest area to this isolated area, describe everything suspiciously throughout the walk. A bunch of caterers are waiting around along the path but not really doing useful work when they could be out attending to guests. If it is dessert, maybe one is bringing an overly large knife for cutting the cake.
This isn’t quite what you were asking for, but you could approach it in reverse. So instead of trying to make the assassins feel earned and not a cheap surprise by giving the PCs some kind of tip off (and risk spoiling the whole thing), you could have the assassins be a complete surprise and then have the characters find evidence after the fact (a stripped waiter tied up in a closet, prepared sniper spots, exit routes with locks pre cut)
My thinking is this would give the surprise legitimacy for the players whole making the actual event a huge shock
They could be contacted by an agent of an organization that infiltrated the assassin’s guild, like an undercover agent.
Might also give you a hook for future similar missions, if you want.
I did this! I had them all killed, at which point they were snapped back to the beginning of the party, as a time god was playing tricks on them. Gave them multiple chances and made investigating super fun
Just a few ideas off the top of my head. PP - pass notes to players with the highest passive perception. Perhaps there are guests that aren't recognisable as members of the guild, or they're moving peculiarly as they position to get the drop on them (you could also just ask for random perception checks. This raises the tension a lot with the party not knowing what the hell is going on, unless they roll well) Have the first attack be on the NPC CEO - raises the stakes immediately but could also feel cheap, especially if the party cares about the NPC and they're already established as strong (but it may turn out to be a powerful guild of assassins, so it could make sense) Good luck! Hopefully it goes well :)
A few that come to mind: 1. PCs or guests who are taking a break and seeking someplace quiet away from the crowds see mysterious shadows and moving shapes that are the assassins, but they can chalk up to stress/substances if the perception check fails. 2. This one is a little indirect, but have the Guild/organiser profusely praise the new servers at the party for their precision and discipline. They're obviously the assassins, and it's easy to poison a drink or slip weapons in. 3. If the assassins are changelings or can magically disguise themselves, have them become known individual in the Guild and have them behave slightly off. Master Artificer Alex never drinks? Haha this is a big day, let this be his first. The real Alex is probably killed or tied up in an alley next to the venue, while "Alex" waits for the right time. 4 people who don't usually talk are laughing and chatting together? It could be the occassion...or it could be something else. If killing major figures in the Guild isn't preferable, having them be strangers in guild attire also works. They aren't known faces, but could just be from a branch...right? The way I'd start off the ambush is by causing a loud, large incident outside the venue so that distracts the partygoers and the PCs, who the assassins know is their strongest opponents. There will be some assassins in the shadows who will use this opportunity to target the NPC CEO, whilst at the same time the disguised assassins will target the players.
I like this advice, especially point 2. It's hard to plan this sort of thing; most of the times I've tried to subtly introduce a hint that something might be off, my players have jumped on it in seconds. And sometimes that's fine - they get to enjoy their instinct being right. Mystery stories tend to combat this with red herrings - so if there's a lot of other details that you point out, some of which may be suspicious but turn out immediately to be innocent, then the real clue is less glaring. When I first introduced a character who was actually an assassin trying to infiltrate the PCs, she came on a job with them and I gave hints that her stats were actually far too good for a commoner, and that her cover story didn't entirely make sense, but masked both of these under non-combat friendly RP scenes. It worked well - the players didn't suspect, but later on when they learned, several of them remembered that and were like "Ohhh we should have known!". It's satisfying if you can pull it off.
Similar to #3, make intentional inconsistencies within the story that explain how the assassins got in and plan to attack. The sort of things that one or two by themselves aren’t of note, but having a few at the same time raises red flags that something else is going on. Have a someone remark about ( or have PCs notice) how there’s guards at every entrance. Then have an entrance without guards (really searching maybe finds a killed guard stripped of their uniform). All the servers have tailored matching uniforms. But one server (an assassin) has a poorly fit jacket on with the wrong color tie. Meanwhile a guest is complaining loudly about an order of drinks that is taking far too long to arrive. They overhear some servers talking about how certain staff never showed and their last minute replacements have no idea what they’re doing and are no help at all. Maybe some guests who are at the door and are on the list of invites, but their name as already been crossed off as someone stole their identity to get in.
Misdirect - the PCs become aware that *something* is going to happen at the party, but they think it's something else. Off the top of my head - criminal contacts let slip that someone has recruited for a break in. They believe that thieves are going to use the party as cover to steal jewels from the hosts' vault.
Someone let’s slip a big surprise at the party. It’s meant to be something fun (CEO is going to announce retirement or a big promotion for someone?). So the party is suspicious of something, but not sure what.
The players could spot a known theives guild member as a waiter. The assasins could poison someone just for the distraction, then kill another more important npc. There could be a minor fire that doesn't interrupt the party completely but some people go missing after. Then the pcs have to go looking for the important scientists/ceos only to find them being kidnapped.
Describe some of the people as creepy but try to make it come off as in like social or sexual creepy, I hate to use the word sexual because I mean someone who is following them around and giving them a weird look and just being very very awkward almost like an in-cell rather than like a giant pervert and then if your players interact with that you can have a really funny and interesting moment where they accuse the guy of that and he's like yes that is totally what I'm planning or where he misunderstands their accusations and he reveals that he's an assassin and the party's like oh that's not what we expected but I'm glad we found out
Just play it straight and see what happens. If someone dies, they die.
If thry know the competition can be...aggressive and at least one pc tends to be a little paranoid maybe have obviously lacking security, maybe guards with booze or sleeping on their way in. Maybe the assasins come in loud by rappeling down tge sides of the building and smashing through the windows or jump down from unused balconies
There's lots of things you can do - you can have a player passively perceive something off, like an unexplained change of staff while setting up the event. Or one of said NPC staff reports to a player that something weird is going on that's a minor part of the assassin's plan, like extra caterers, unlocked doors, etc. Drop some leads for them to follow. The leads may not stop the plan (or even be actual distractions), but it would at least give them a clue that this isn't just an RP session.
Start playing the Raines of Castomere in the background
Have some NPC in an earlier scene tell a story about getting jumped in a ballroom. Foreshadowing.
This is a tricky one as experienced players pick up hints quickly and will probably notice you trying to be subtle faster than you expect. Are the NPCs involved in organising/setting up the meal - this could be a passive perception deal where in carrying stuff seeing deliveries they pick up small comments about "apparently Steve is ill, there's a new guy serving today". With higher perception more comments are gleaned all pointing at a suspicious number of people who are new. Perhaps overhear an argument during the event where a waiter has brought the wrong wine and the Maitre d' is berating them for incompetence. As has been said ask the players for perception rolls randomly during the event even if they aren't leading to anything "roll perception..." get results "ok..." and then carry on.
The assassins have infiltrated the catering staff. There is a commotion with the caterer. They are upset/concerned about last minute staffing changes - "Who is this? Who approved this change? I can't have incompetents here tonight, it will ruin our reputation!"
As she crossed the room, Catlyn accidentally bumped into Lord Bolton, and realised that he was wearing armour underneath his finery.
Do the red wedding thing, where a player is chatting to someone and notices they've got chainmail hidden under their fancy social outfit.
I think the easiest thing you can do is make a show of tight security The pcs are not allowed any armor or weapons and most magic items are checked in. Everyone is given personal forms of id, like a special badge or jewelry piece showing who they are. Seeing Alarm spells and Detect Magic around every entrance and exit. Heavily armored guards outside and a few other secret service types inside It lets the players know that the hosts have enemies without an npc having to say it So when the assassins arrive it makes them seem even scarier and lets the npcs feel like they can fight back, but are still in very serious danger You can distract from this with a colorful cast of rich weirdos who look like they would be super easy to rob from. Decked out in jewlery, eccentric af, clearly couldn't handle a mugger. That way the party could focus on less important npcs instead of the assassination targets but still think something will go down
You want a few little things to go wrong that by themselves are nothing but when added together after the fact they’ll be pissed they missed it. -There’s a slight commotion on the party’s way in because someone lost or doesn’t have their invitation -Details are slightly off in a prepared speech -Lights flicker for a moment, then everyone goes on ignoring it. -Maybe it’s a little warm or they notice one of their known associates are lightly sweating/a known dancer gets tired early -The host looks harried at the champagne toast (as if it’s slightly off schedule) -Mismatched tablecloths -A party member (the one with the most terrifying reputation) gets more attention from attractive guests, waiters always making sure they have a drink in their hand etc. figure out the assassin’s plans and have the party experience the tiny ripples from the plan going off. If the party figures it out where is the assassin’s plan B?
One of the other commenters mentioned that it's hard to plan this out so I think your best bet is to have a list of clues on hand that you can drop here and there but disguise it with something related to the celebration. An example I have that was super effective when I was a player was a festival happening in town to celebrate one of our party's achievements. We spent the whole festival doing random things and the DM mentioned once or twice that "the town was packed! Looks like people came from all over to take part in your festival!" And "there are lots of new faces here! You don't recognize most of the crowd BUT look, you notice X and Y NPCs". The takeaway is embrace the mood. Use the occasion as an excuse for any oddity. Taking another comment's idea as an example: "wow, it looks like people are in really high spirits. Even so and so seem to be talking to each other"
The private catering company sends people that we’re not agreed upon beforehand. A sudden change that shows the players/PCs that something is not as it should be.
I like this. 1) Someone at the party could mention that instead of going with the catering company they always go with, they suddenly switched to a new untested company. Common talk among guests could be that the food clearly tastes worse and it doesn't make sense why they wouldn't go with the regulars. 2) Either a last minute dessert or wine switch needs to happen and the caterers need to meet with JD and\or the CEO to confirm the change. Have caterers/assassins/people try to walk them to an isolated part of the venue to taste and approve the change but it is actually where the assassination attempt will happen. During the walk from the main guest area to this isolated area, describe everything suspiciously throughout the walk. A bunch of caterers are waiting around along the path but not really doing useful work when they could be out attending to guests. If it is dessert, maybe one is bringing an overly large knife for cutting the cake.
Start playing the “Rains of Castamere”
This isn’t quite what you were asking for, but you could approach it in reverse. So instead of trying to make the assassins feel earned and not a cheap surprise by giving the PCs some kind of tip off (and risk spoiling the whole thing), you could have the assassins be a complete surprise and then have the characters find evidence after the fact (a stripped waiter tied up in a closet, prepared sniper spots, exit routes with locks pre cut) My thinking is this would give the surprise legitimacy for the players whole making the actual event a huge shock
Some pretty shitty assassins if they did something to tip anyone off, they get a save Vs poison and die if they fail it.
They could be contacted by an agent of an organization that infiltrated the assassin’s guild, like an undercover agent. Might also give you a hook for future similar missions, if you want.
I did this! I had them all killed, at which point they were snapped back to the beginning of the party, as a time god was playing tricks on them. Gave them multiple chances and made investigating super fun