In my campaign, one of the PCs is an assassin.

Before the game started, I gave the player a list of assassination targets. One of the targets happens to be friends with the party's warlord. It's been interesting, as there have been a few points where the assassin could have killed his target, but not without alerting the warlord.


The player would like his character to sneak off alone in the night during an extended rest, or at some other point when the part is split for a while, assassinate the target, and come back without anyone being the wiser.

This seems like a good plan to me, but I had a conversation with the player, and we're both concerned that roleplaying this event would result in me and him playing the game while everybody else sits and watches.

Possible Solutions

I've considered framing this whole event as a skill challenge so I can just have the player roll a few dice, find out what happened, and get back to the action. We don't really like skill challenges though, so I'm a little hesitant to throw one in just for this.

I've considered finding something for the rest of the part to do in the meantime, like giving them a puzzle to solve they have to talk about, or putting them in a fight with an enemy I don't have to think about much, something like that. This might just end up being chaotic and poor for everyone, though.

I've considered having a session with just me and this one player to determine what happens, and then informing the rest of the group when we play our normal session. This is not super-convenient, but may be the most fair to everyone. One serious problem with this approach is the in-game timing of the event. We're halfway through a session, the party decides to take an extended rest, the assassin wants to go assassinate... and I tell him what? "We'll do that this weekend. Just assume you didn't die and came back so we can continue this session"?


Have you ever done something like this in one of your games? How did you handle it? Did your approach work? What works best?

We're playing 4th edition Dungeons and Dragons, so keep that in mind if you have a system-specific answer, but as this is mostly a question about managing the table I'd be happy to hear answers citing applicable experience from any edition or even other games.

Note on the Nature of the Assassination

I don't want to make this question so specific that it only applies to my situation, but I was asked for more information on the nature of the assassination in this particular instance.

The assassin is a monk serving the god of death. The assassination target was given to him by his monastery, and originated as an order from the god. This is one target on a list, and killing the targets on the list is the character's primary goal.

This particular target is not dangerous, just a harbormaster, but others on the list are extremely dangerous.

  • 4
    \$\begingroup\$ What is the goal of this assassination? Is the target powerful enough that it's a tough challenge for the assassin, or is it not so much about whether or not the assassin can succeed, but whether he can do it without alerting others? Is this just a piece of backstory and roleplay, or is it a crucial part of the campaign (or at least the assassin's story?) I think deciding why this sideplot happens might factor in to how you could best play it. \$\endgroup\$
    – Erik
    Commented Apr 1, 2015 at 7:59
  • \$\begingroup\$ @Erik I'd like to see answers general enough to apply to others' situations, but I added a note on my particular situation if you'd like to speak to that. \$\endgroup\$
    – DCShannon
    Commented Apr 1, 2015 at 18:19

11 Answers 11


Arranging a separate session is both most convenient and most effective.

It's actually most convenient, because it inconveniences two people (you and the player) a little bit, while avoiding inconveniencing even more people (everyone else) by having them sit around doing nothing. Arranging a separate session might be slightly inconvenient for you two, but for your group as a whole, it has maximal convenience.

In practice, this also works the best: you have freedom to focus on the action. If you're doing this while people are waiting, eventually you get distracted by the clock and anxious to get back to them, and this impairs your ability to focus on DMing this side-bit properly (which ironically slows it down). With one-on-one focus you can blaze through a surprising amount of play in very little time.

Options for playing side sessions

In my experience, the easiest way to arrange this is to play remotely. I've run side-sessions over the phone, either when using a system that doesn't require a lot of visuals, or when the side-thing itself just didn't require visuals. For games that do require visuals, you would get the same convenience of a voice call by using videoconferencing software (Skype, FaceTime, Google Hangouts, etc.). However,visuals aren't as necessary as they seem even in games that are designed to use a combat grid, so voice-only sessions are more possible than is often assumed.

If remote isn't an option though, getting together in-person can be surprisingly convenient anyway: you only have two people's schedules to coordinate instead of a whole group, making it more flexible; and you can get more done when you're playing one-on-one, so the session will probably require less time than you expect.

Session synchronisation

Ideally, you would arrange the main game so that you end the session at a point in-sync with your plans for the side-session, such as during a night's rest (as you mention in the question). Having the in-game events sync up with the out-of-game session boundaries is nice.

It's not necessary, however. You can just as easily set the side-session at a point in time where it could have already happened. If your party is in the wild and the last session ended with them mid-combat, you can still set your side-session back in time a little bit, during the last long rest they had, as a flashback. Doing this may involve a few artificial constraints: obviously the PC needs to survive their little secret outing, and lesser changed details like new gear and injuries need to be somehow not obvious, in order to explain why nobody in the party noticed the changes after.

These kinds of things can be arranged with clever DMing though: you can have an injured solo PC stumble upon a Good Samaritan healer at the end of the side-session, and other such contrivances. For a one-off side session, your player won't anticipate these contrivances being necessary (and so won't be tempted to metagame them). Even something extreme (such as PC death) can be contrived to go unnoticed: in the extreme example of the PC dying during the flashback, just let the PC die and don't retcon their apparent aliveness, but instead reveal that their companion has been a revenant or corporeal ghost of some kind after the next time the PC syncs up with the main session. That example is not something I would recommend as a regular occurrence, however! The point is only that unexpected fallout from a flashback can be accommodated with a bit of though and creativity without needing to retcon the in-world events between the time of the flashback and the "current" main-party time.

So you have a lot of freedom here. If you can arrange for the side-session to be played between real-world main party sessions, that is ideal. But if you can't, just make it a flashback during a near-past likely opportunity, and trust that the flexibility of the fantasy genre can give you all the tools you need to patch up any discrepancies that emerge from the side-session.

  • 2
    \$\begingroup\$ If you do introduce a Good Samaritan or other such contrivance, then you can introduce an alternative cost such as incurring a debt (the not so Good Samaritan) or replacing a trap that might have killed the character with one that enchanted them with a curse (perhaps one that allows the heir to track them down over time). \$\endgroup\$
    – Quentin
    Commented Mar 31, 2015 at 23:12
  • 15
    \$\begingroup\$ The solo session can be set in the future instead of the past. That way it can be slotted in to any appropriate rest period at a later game session (player tells DM in-session that this rest is when it is done, and both apply the changes they have keep track of in the character and world that resulted from the one-on-one session. There is no need to retcon, have contrivances like a Good Samaritan healer, or constraints like the character surviving. This allows the entire party to respond to any in-world result (character injury, death; city guard alerted to search for the assassin, etc.). \$\endgroup\$
    – Makyen
    Commented Mar 31, 2015 at 23:38
  • \$\begingroup\$ Good points on the retcon and contrivances. This is probably what we'll do. I'll mark an answer after it happens, or after a while if it doesn't. \$\endgroup\$
    – DCShannon
    Commented Apr 1, 2015 at 0:45
  • 2
    \$\begingroup\$ @Makyen could you make that into an answer? It's a novel idea and should be preserved beyond the frequent comment deletions. \$\endgroup\$
    – Arkhaic
    Commented Apr 1, 2015 at 9:05
  • 1
    \$\begingroup\$ We had this session just the other day. It went pretty well, and I think the results will improve the next group adventure. We didn't have to retcon, as I was lucky enough to be able to end the previous session right after the character snuck off. \$\endgroup\$
    – DCShannon
    Commented Apr 20, 2015 at 18:09

You are running into a common problem, and not one that has an easy solution, as it depends on the nature of your group. Let me offer you some options.

The Solo Session

Meeting up with your assassin, either in person or over some form of RP conducive communication tech (Skype, chat room, what have you), you have a micro-session for the assassination, which will take place sometime within a week (in game time) of the last game break. This will allow you to give the story arch the time and attention it deserves, while leaving the actions and results mysterious to the other members of the party until they're revealed in game, without having the party sit and twiddle their thumbs for an hour.

  • Pro: Defense against metagaming fueled reprisal against the assassin or his player
  • Con: Requires more time spent gaming that you may not have.

The Skill Challenge

Have a little flow chart of options, and have the assassin roll his way through them to success or failure in five minutes.

  • Pro: Fast and doesn't need an extra session
  • Con: Boring and under cuts the importance of what is being done.

The Solo-Adventure

Rather then running a solo session for the assassin, you prepare the warlord's friend, his house, the neighborhood, locals and guards and what have you. Then you grin when the party gathers and tell everyone but the assassin to put their characters away. Then distribute NPC sheets, having the warlord play his friend, and have the Party roleplay the NPCs during the assassin's mission. (Be sure to enclude enough NPCs for people to switch out if an NPC they were playing dies, is removed from the enviroment, is knocked out, etc)

  • Pro: A very memorable session that doesn't leave anyone out.
  • Con: Metagaming Danger, both during the play and afterwards.
  • 8
    \$\begingroup\$ +1, The solo adventure is a neat idea. I might suggest that and see what everybody thinks. I wouldn't want to just spring it on them when they showed up thinking that they were going to play their own characters unless they knew it was a possibility. \$\endgroup\$
    – DCShannon
    Commented Apr 1, 2015 at 0:43
  • \$\begingroup\$ Fair point... I am basing things off my group, where we have 3 GMs who often bully each other into making sure there will be a game prepped, even if there isn't an easy way to determine what game will happen when. \$\endgroup\$ Commented Apr 1, 2015 at 3:26
  • 1
    \$\begingroup\$ +1 for suggesting the Solo Adventure, letting the other players run the NPCs is great for drama. I think there's a chapter in the DMG2 on running Vignettes that might offer more good advice on how to do it. \$\endgroup\$
    – Erik
    Commented Apr 2, 2015 at 9:02
  • \$\begingroup\$ @ Erik: It might, but I skipped from 3.5 straight to 5th, so my answer was the best I could craft it to be system-generic. \$\endgroup\$ Commented Apr 2, 2015 at 18:32

Let the uninvolved players control the opposition

If nothing will happen while the PCs sleep and the assassin heads off to perform the assassination, continue playing, but give the players whose characters are sleeping control of the foes and have the players defend the assassination target. Then make that engagement fast and simple.

This means perhaps revealing vital intelligence about the opposition to the players, but the players likely know most of it anyway if they've already previously engaged the foes. While this sometimes baffles new players ("Wait, I'm a what now?") and long-time players ("What's my motivation?"), the players in my campaigns tend to adapt to such a situation quickly, taking but a few minutes to familiarize themselves with their new roles ("You're an orc. You're on guard duty. The warlord will kill you if anyone makes it into camp.").

I admit that my campaigns are pretty transparent. I abandoned the step-outside-and-talk model when it started monopolizing sessions. Players now stay at the table and describe publicly their characters' private deeds. It's reigned in player-versus-player and created a good shaming mechanism that prevents the DM from having to indulge in secret one character's or player's debauchery. (Well, the debauchery of those who feel shame, anyway.)

The players who frequent my table are experienced role-players, quite capable of compartmentalizing. They discard easily knowledge of events in which their (primary) characters weren't involved. I can imagine this technique failing in a beer-and-pretzels or metagame-heavy environment. Further, I use a show-up-and-win model for advancement rather than numerically tracking each individual PC's advancement, so controlling a monster for 30 minutes while another player controls his own character doesn't cut into the monster-controlling player's character's advancement.

Giving control of the opposition isn't for every table, but many alternatives require time that in my opinion is better spent making the game better for everyone involved rather than one player.


Is the player of the assassin interested in not having the other players know, or just the other characters?

If it's the first, as has been suggested, try doing a separate, one on one session for the assassination mission.

If it's the second, talk to the other players about arranging a special session where the assassin sneaks away and they take on other roles for a while. Give them roles as the target's elite guards (or even the target), and you just handle the storytelling part of it.

If that works out well, consider doing similar vignettes for other characters in a similar vein; the fancy Bard wants to go to a dinner party and sneakily glean information from someone? Make some information sheets for the other players, and let the roleplay happen. Fighter wants to go out and do an all-fighting, undead-slaying graveyard run to prove he's worthy of the ancient armor of Shinimus the Sunbaked? Hand the other players a few necromancer sheets and a limited number of undead minions to throw at the PC.

It's more work for you in prep, certainly, but that kind of personal attention makes for an incrediby memorable and satisfying game. Just make sure the group agrees on the goals. Is it a hard task that the PC has to be smart and lucky to get through, and if he isn't, what kind of consequences will there be? Is it a chance for the hero to just be an unmatched paragon of whatever she does (warrior wading through an army, assassin effortlessly sneaking to a target and silently dispatching it, cleric charismaticly converting an entire village to worship the Fire Goddess instead of the Sun God)?


Concurrent Encounters

Twice in my 4e campaign I had situations where a person would be in in single-combat. I solved the issue of splitting the party by running both encounters concurrently, with everyone still playing at the same time, everyone in the initiative order, but with the individual PC in a different location dealing with a different threat.

The second instance is more relevant to the OP. I had a player who was playing a half-orc ranger who really just wanted to be a dual-wielding assassin. The party was underground preparing to assault a duergar mining camp that had been taking slaves from the surface. The sneaky ranger had told me ahead of time that he wanted to break away from the party and sneak in to assassinate the leader.

So I let him. Right when he was standing above the sleeping form of the duergar foreman the rest of the party started raising hell, and the foreman woke up. I had everyone, even the ranger roll initiative. I ran the encounter as normal, with most of the party in the middle of camp fighting guards and scouts while the ranger fought against the huge, naked duergar foreman. It was tough, but he won out, and then came up with a clever way to make his personal win help the rest by demoralizing the remaining duergar.

The first time I did this was actually a formal duel, where the mastermind behind the reason for the duel lured the remaining party away from where they were spectating and then ambushed them. I ran both encounters simultaneously, and no one was bored. Everyone had their part in advancing the story. Personally I think it's best if everyone can share in all of the cool moments, rather than letting some players hog the special stuff, even if it's not taking away from normal game time.

  • \$\begingroup\$ This seems reasonable for when you have concurrent encounters, but running off to assassinate someone is going to be mostly exploration with little to no real combat. I'll keep this in mind if the party can somehow interfere with his adventure, which I had not considered. \$\endgroup\$
    – DCShannon
    Commented Apr 1, 2015 at 2:41
  • \$\begingroup\$ We were playing DnD 4e, and one of the main unspoken rules of that version is "Don't split up the party". There should always be a way to get everyone involved, and even exploration segments can be run concurrently. \$\endgroup\$ Commented Apr 1, 2015 at 2:55
  • 1
    \$\begingroup\$ "Don't split up the party" isn't so much an unspoken rule as explicit advice that my playgroup intentionally ignores all the time. The party decides to split up regularly, and it usually goes pretty well for both the players and the characters. The only thing that's unusual about this situation is that the rest of the party is sleeping and he's trying to hide the fact that they even split up at all. \$\endgroup\$
    – DCShannon
    Commented Apr 1, 2015 at 3:00

Have some mindless good fun

I realize that this is not a generic solution for everyone. But it can work quite well if you get the chance. What you need is a group of people that has a common agreement on mindless fun. And a place to do so.

For example, when I was in school, our roleplaying groups consisted of 5-7 people and the group was split up regularly for periods of time. Because the group wanted it or because the adventure dictated it or because the rules dictated it (Decking, Hacking and Netrunners in Shadowrun/Cyberpunk worked always alone in so called "Runs" because no other character could influence the cyberspace). So what we did is put a TV and playstation in the other room and whenever people were not at the table roleplaying, they sat there and played Tekken against each other. Mindless fun that you can always interrupt when it's your turn at the table.

You need the location and you need the "hardware" (gaming console, playing cards, billiard table, whatever floats your boat) and you need a common understanding what is fun. You may not have that now, but who knows, if you ask your people, it might be easier than you think.


I'd propose something a little inspired by the narrative gimmick used by Prince of Persia: Sands of Time (and other games in that series), in which the destination is pre-ordained but there is entertainment to be had in the telling of the story. As unreliable narrators relating how the assassination went, past tense, both you and the Assassin have opportunities to retcon the story and make adjustments along the way in a non-linear manner, in a way that can be performed as a mini-session of yourself and the assassin to entertain the other players.

The basic goal is to compact the assassination story into a sequence of shorter, representative challenges and abridge where necessary (made possible by the fact it is a related vignette and not actual action). You may wish to give your Assassin a number of retcon tokens that allow them to make narrative changes to eschew things in their favour and add unique gameplay flavour; ultimately the goal is not to change the outcome, but the side-effects of the assassination.

Where the players can really feel involved is in those side-effects; make them potentially relevant to the other players (and thus an incentive for the assassin to be relating the story as they are). While the players themselves are not directly included in the action, it makes the action relevant to them and gives them investment in the sequence. These potential side-effects could be very general and effect the whole party, or could be very individual.

Naturally, you probably don't want to structure this in a way to last an entire session, but if done well it could be an entertaining diversion from the normal flow of play.


As long as the amount of solo time spent isn't excessive, and/or the other players have something fun to do at the same time, I recommend and encourage solo and split-group activities. Solo and split activities often make sense, can create interesting situations, challenges and opportunities, add variety, and can lead to good character development and roleplaying that would not happen if everyone in a group were always present everywhere (or if solo activities are required to be handwaved or shortened). If solo/split activities aren't allowed because of the real-world reasons, then it creates an artificially weird constraint where PCs are discouraged from doing things outside a group, which can be very unnatural, gamey, silly, etc.

Other players can have fun:

  • Watching the action, if that works for your play style, etc.
  • Wondering what each other are doing, when you actually split the players.
  • Playing opponents, if you do that.
  • Doing something else (scheduling limited-player sessions, or breaks), if you have multiple GM's, or other games to play.

I have allowed and encouraged this, and played in many games where this was done a lot, and it was rarely a problem for me or the other players. If it's really going to take a long time, the main thing is to let them know so you don't waste other people's time, especially unexpectedly.


Does it have to be a solo mission?

I once ran a mission where a PC was interested in stealing a prized jewel and was the only one with the skills to pull it off. In your case it sounds like your assassin also is the best suited and most inclined to pull off the kill. That being said, it doesn't mean the others can't help. The mission would focus mainly on what the assassin is doing, but is the harbor master protected by anyone? If so, why not have the rest of the party distract the guards with a keg of dwarven ale? Or create a ruckus outside to get their attention and start a fist fight with them. The could help in other ways as well, what is the likelihood the assassin would be suspect in the targets murder? Perhaps the other players could be off creating an alibi for the assassin, maybe taking turns dressing as him at a public event, being "seen" with the other characters so none of them could be fingered as having the ability to commit the murder. There could be several checkpoints along the assassins mission that would alter the whole thing depending on what the other players do to help (or hinder) the assassins progress. That way the story is mainly focused on the assassins mission, but the others can get involved, and have a hand in the outcome. It should also keep the other players more engaged to the story wondering how, and when they would come into play.


Unless it is going to take more than 10-15 minutes to run this solo mission, just run it while everyone else takes a pizza break.


To elaborate further, in the gaming I've done, there inevitably comes a point in any session when people want a break to grab a bite to eat, go to the bathroom, smoke a cigarette, etc. Taking such a break when the party has gone to a sleep for the night is a great time, in my opinion, to run this kind of small one player activity.

  • \$\begingroup\$ Can you elaborate on how this meets the asker's needs? The question isn't when to run it, but how to run it. See: "Have you ever done something like this in one of your games? How did you handle it? Did your approach work? What works best?" \$\endgroup\$ Commented Apr 2, 2015 at 13:23
  • \$\begingroup\$ @PurpleMonkey The problem, as the OP states it, is "we're both concerned that roleplaying this event would result in me and him playing the game while everybody else sits and watches." How does my answer not address that issue? \$\endgroup\$
    – Kevin
    Commented Apr 2, 2015 at 17:25
  • \$\begingroup\$ @PurpleMonkey Although this answer won't work for my group, as we eat beforehand and have no significant breaks while playing, when to run the adventure is big part of how. \$\endgroup\$
    – DCShannon
    Commented Apr 2, 2015 at 17:39

I almost didn't respond since the top ranked answers were so good, I especially like the soloadventure with players taking NPC roles.

However, if the player knows that he needs to accomplish a goal (assassinating an NPC from a list) it is the player's responsibility to accomplish the goal. You have stated that you asked the player which NPC he will target, to me that sounds like the player is not actually taking the initiative to accomplish his primary campaign or session goal. When determining your list of targets you should have a simple itinerary so you can allow the player to determine his best course of action over multiple play sessions. (let this be main point #1)

From what you posted, you have a variety of targets, each with differing degrees of difficulty. Make a matrix (even if it is just for your own use) to describe a skill challenge for any given target along with rewards/penalties. The key to a memorable session is to make the outcome of decisions apparent to the players. So, the player chose a specific target... that decision should have been roleplayed in a conversation between you and the player. Then you can step out of your roles and determine if more sessions are required.

What I have experienced in playing with a group of Army buddies (we had bi-monthly sessions with multiple DM's, in a shared campaign world, but each DM was responsible for story threads he/she initiated.) Was to handle this situation out-of-group discussions and skill checks.

What I recommend to your situation, is a group session where the skill checks center on evading detection from the rest of the party. If they are asleep at 2am, then the assassin may only have a 3 hour window of opportunity to achieve his goals. You could include a D20 random event table to add excitement. Add another skill challenge to determine the outcome of the assassination encounter.

Also bear in mind that characters may have godlike perception, and may be able to determine that the monk was gone or that he is behaving oddly. So having all players make a perception check in the morning is a good idea. The suspicion will add flavor to having a shady character in the mix of characters.

Finally, this allow you even more opportunity to reward(punish) players for RP (lack thereof). In your game notes, keep track of players that have done hidden actions and those which have become aware of them. A simple spreadsheet matrix with players & events as rows and Players as columns will allow you to use 'x's to track who knows what. If you apply an XP penalty to people acting with knowledge they could not have, you encourage players to better track their knowledge.

while an XP penalty may seem punitive (here is point #2) you have a situation in your gaming session (with the assassin monk) where one player wants to (or must) hide a subset of his actions from the rest of the party. This may seem cool to the player, and it may seem cool to you (as GM) and the player; logistically, however it makes a situation where you have to generate more content and players have asymmetric session time. That is all players play for a different amounts of time which should result in different amount of available experience for people.

Finally (point #3) to the specifics of an assassin god. You have an opportunity to develop your campaign more by answering some fundamental questions about what temple objectives are being forwarded by specific assassinations, what is the role of the player in the temple, and the logic driving target selection. If the player is low level you can handle this by simply requiring 'innocent' blood be spilled with the god's favorite weapon, during the period of every full moon. Since there are generally tons of targets in a city, the player simply needs to be in a city during the time frame.... this will be an issue during long wilderness or dungeon expeditions. The player may then suffer some sort of penalty until he regains the god's favor.

The intent of point #2, and #3 is to reinforce the reality that anti-social and amoral behaviors do not easily coexist with a group that requires all players to share a strong bond of trust. For roleplaying sake, you have anti-social options, but certain concessions must be made by the players to allow a group dynamic to succeed.

  • \$\begingroup\$ There's some interesting and potentially useful advice in here, but very little of it actually applies to my group or this particular situation. The player isn't choosing targets. I gave him a list from his temple when he made his character, and I already know exactly why all the targets are to be killed and how they fit together. We almost never mess around with skill challenges, choosing to RP these situations instead (with a couple die rolls when they're relevant). The player made up a reason to be gone, so party's perception is irrelevant. \$\endgroup\$
    – DCShannon
    Commented Sep 1, 2015 at 20:29
  • \$\begingroup\$ All the characters get the same XP every session, regardless of their or their player's actions. The party does not share a strong bond of trust, and we're all surprised the assassin is still alive. Anti-social and amoral behaviors not coexisting with the rest of the party is kind of the whole point of the character. When the character was created it was known that there would be a lot of friction with the other characters, and he wasn't expected to last this long. \$\endgroup\$
    – DCShannon
    Commented Sep 1, 2015 at 20:31

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