Dragon Encounters

Making dnd combat fun, finding monsters that fit together, monster tactics and strategies, and other ways of using the monsters of dungeons and dragons

IMP: How to Make Really Bad Bargains


Combat rating 1


1 Imp (CR 1)

2 Winged kobolds (CR 1/4)


Combat rating 2


1 Imp (CR 1)

1 Fire snake (CR 1)

4-5 Cultists (CR 1/8)


Combat rating 3


1 Imp (CR 1)

1 Wererat (CR 2)


Combat rating 3


1 Imp (CR 1)

3 Magmins (CR 1/2)

1 Yuan-ti pureblood (CR 1)

How to Use – Warlock Companion

(I’ve already gone through basic advice on running a familiar, or any kind of NPC that accompanies the PCs on their quest, in the quasit article. I’m including that information here is a spoiler, so that it’s accessible to readers who want it, and so that readers who already read my quasit article don’t have to read it again here.)

Anyone reading this article knows that warlocks have a few special choices when selecting their familiar. Many, probably most, people think of familiars as just a number of new abilities that come in a package. While this probably is the main point of a familiar, you are also adding a new character to your party, and they come with their own character traits.

You don’t want to overuse this feature. The players and their characters deserve the spotlight, and one of the worst mistakes a DM can make comes when they place a character of their own into the party. (Since the DM is already running the show, their character knows anything of importance, always makes the right call, and quickly ends up running the show.} But the occasional light touch can add a nice touch of personality to the game, and liven up the world.

Personal Story: I came to this realization as a player. I was playing a ranger beastmaster. We were hiding in the trees to avoid notice from the enemies, and since my leopard beast companion couldn’t do that, one of the other players pushed for me to leave the leopard behind. A short time later, that PC happened to be passing near my leopard, and the DM narrated how the leopard laid back his ears and growled at the PC. (He afterwards apologized for controlling my character, but I thought it was great. Had I done it, I would have just been seen as holding a grudge. He made my beast companion come alive.)

Before we get into specific ideas for how to use the quasit, let me give a quick list suggested rules that I would recommend with all familiars, beast companions, and NPC allies in general. (If a quest revolves around an NPC, you can use that NPC a little bit more, but they should still take backstage to the PCs. Furthermore, I would suggest making such a quest a short one. Either that, or having them separate, or become separated, from the NPC midway through. The overall goal being not having them spend too much time with the NPC.)  

Give the ally a brief chance to speak, but only about once a session. [The first session or two that he’s with you he can have a little bit more time, as he’s new and exciting, but only a little bit more.]

By far the best time for the ally to voice an opinion is before the players start discussing it. Do it afterwards, and it looks as though you’re taking sides. My ideal would be for the NPC to provide new information, either in the form of something he noticed or something he remembered, and give an opinion to go with it. [You’ll obviously have to make clear what’s the new information and what’s the opinion.]

I would suggest that the NPC be right at least one third of the time, and wrong at least one third. (The remaining third can be set either way, or split down the middle. I said thirds to give you some flexibility.)

While advice is acceptable, compliments are almost always welcome. [Requests are okay, but they tend to be time consuming. See next paragraph.]

If you decide to let them do something that will have consequences for the party, keep those consequences mild. They should never save the day. If they’re causing problems, the problems should be solvable fairly quickly. Familiars and beast companions are given to the character as part of their powers, and it’s unfair to impose a penalty on them for it. [With other NPCs you have a little more slack, but the players will quickly come to dislike them if they make too much trouble.]

If these actions affect the willingness of other NPCs to help them, or involve the NPC themselves being reluctant to help them, have a plan beforehand for how they can persuade the NPC, and how they should proceed if they can’t persuade them. Going in without a plan will very likely end with the players arguing back and forth with the NPC until one side gives up in frustration.

An imp will be looking for ways to corrupt its master, as well as anybody else that it can. To achieve that end, it will look for ways to suggest evil deeds that have some chance of being persuasive. For example, to rob an NPC adventurer of some of his healing potions. After all, surely the PCs quest is of higher priority.

You can also use this to suggest to them deeds that they might have done already. For example, after an NPC companion dies on a quest, the imp can suggest to them that they keep the possessions that they already took for the corpse. After all, it’s not like the relative would ever have been able to get the items back from the dungeon. While this is something they might have done anyhow, coming from the imp it will seem evil if they don’t return the object.

The imp will also be looking for temptations to place before them. You can have it report to them on items that it knows they might want, but which are currently in the hands of people who won’t want to give them up, thereby tempting them into stealing them.

You could have it report to them information that calls the trustworthiness of specific NPCs into question, thereby prompting the players to treat them badly, perhaps abandoning them in a dangerous area.

You could have the imp make it seem like the NPC had an evil motive for doing something, thereby motivating them to take revenge, or at least to not help an NPC in need, despite the fact that the NPC might not have intended to do any evil.

The imp may also encourage them to befriend, or at least deal with, evil creatures. For one example, there is an item that they want in the hands of a hag, or of a crime lord. They are willing to trade the item to the PCs for something that will cause harm to innocent people. (In the crime lord’s case, for something aimed at expanding his power.) If the players refuse the trade, the imp can wait for opportunities where obtaining the item is really tempting, and then remind them about it, along with providing arguments that it’s for the greater good.

The imp can also find out about the item, and propose the trade in the first place. Obviously, the best place for him to suggest dealing with is the Hells. He’ll point out that just by taking him as a familiar, they are dealing with the Hells, so what’s the difference doing it a bit more.

In the same vein, if there’s a cursed item, perhaps one that will kill its owner if them take it from them or if they use it, or one that will release monsters, flood, or drought onto a community, or one that can only be acquired if some dark deed is done, the imp will be urging them onto that path.

This was already covered above, but I just want to remind you that interference by the imp should be well spread out. Neither you, not the imp, want the players to get used to just ignoring him advice. Accordingly, he should offer it infrequently. Also, he should speak up once [per time]. He shouldn’t keep pushing the PCs to accept the advice, or the players will feel that they’ve been forced into it. Realize that with D&D, so long as you are talking, nothing else can get done.

Dealing with Corrupted Players

The big risk of using this approach is that the players might actually follow the imp’s advice, and start doing immoral deeds. If they do it on rare occasions, you can probably ignore it, but if they keep doing it, you’ll have a problem on your hands. There are three basic ways to deal with it.

The first way is to expose them to the results of their corruption in a way that they won’t be comfortable with. Let them meet the person whom they’ve condemned to poverty, or the relative or friend of the NPC whose death they caused. Avoid being too direct, and having the person tell them off for their misdeeds, as that will just cause resentment at you, their DM, for putting them into the situation. Instead, have them get tangled up in the plot. It the players need something from them, you can slip in a few descriptions of their predicament without being too obvious about it.

You can also have them need help, and put the players in the position of deciding whether to help them. I would make the help needed be something that will be costly to the players to do, not just five gold pieces or such, and make it that the help won’t fully repair the harm that they already did.

Having someone worrying about their loved one and not knowing what happened, while the layers know what happened, is also a very powerful way to make them feel guilty.

The second thing you can do is create actual problems for them as a result of their misdeeds. Perhaps a good-aligned creature is unwilling to help them, or to meet with them, as a result. The aid that they hold back should not be something that the players absolutely need, or there should be another way for them to get it, so that they don’t get stuck not knowing what to do. You never want your players to be stuck in such a way.

You can also have the good alignment creatures/NPCs come after the PCs. When you do this, you’ll want to have them be too strong for the players to handle, or they’ll end up getting killed. (You’ll have to provide the players with the means to escape or hide, and/or you’ll be blocking off areas of the world map that they can’t enter.)

You can also combine the first two ideas. Have the widow of the dead NPC possess some knowledge that they need, but her son, lacking the good influence of a father figure, went off and joined a cult or criminal organization. She’s not willing to help him unless they first help her bring her son back. Alternatively, the child can have gotten kidnapped, and they need to rescue him. The item they need no longer belongs to her, as she was forced to pawn it to make ends meet. You can hopefully come up with other ideas as needed.

I should mention that you don’t want to make this side quest boring. Your goal isn’t to punish the players, it’s to make them rethink what they’ve been doing. Also, they’ll find being forced away from the main plot frustrating even if the side quest is incredibly interesting.

The third idea is to discuss the situation with your players out of the game. Tell them your problems with the way the game has been going, ask them what they think, and be prepared to accommodate their suggestions, even if they weren’t exactly how you envisioned your game. It is possible that your players interpreted what you had the imp advise them as you saying that such actions are totally legit. After all, you were the one talking.

More warlock companion scenarios

The imp will also be happy to talk to other NPCs it comes into contact with. Have it manage to sucker an NPC, preferably one that the players know, into making a bargain of some sort with it.

I would be careful of having the imp talk a friendly NPC into selling their soul. There is no way for the players to undo that, so it won’t lead anywhere interesting and will leave a bad feeling in everybody’s mouths. You could have it talk someone into making a hard to accomplish bargain, in the hope that it will be able to collect their soul when they fail.

Since the players won’t feel like it is their fault, nor should they be penalized for taking an option offered to them by the Player’s Handbook, the quest to help the NPC fulfill their bargain should be short, probably not more than a single session, the tone should be kept light/comical, and the imp should be suitably frustrated with them. If its end of the bargain is something that it very much doesn’t want to do/pay, and it only made the bargain because it didn’t thing it would have to, everybody will feel like that is poetic justice.

You could have it bargain with an NPC who is both already corrupt and unpopular. In that case, the players won’t necessarily save him, and his downfall can provide a twist on the plot at a later date. Just make sure he is unpopular. Fiction narrative is full of rogues who are popular, ranging from Robin Hood to Han Solo, and for them to lose their souls won’t be appealing.

To take advantage of the imp’s shapeshifting abilities, set a scene where they have to discover some information, or steal an object. The NPC holding the item is too powerful for them, or someone whom killing would have political consequences that they can’t afford, so they’ll have to be sneaky. Add in a spell banishing invisibility from the area, or have the NPC have truesight or some other way to see through invisibility, and you have the makings of an encounter that needs the imp’s shapeshifting.

Just don’t use this idea if your party has a rogue, as the rogue will justifiably feel undercut. If, on the other hand, completing this job requires the rogue, and the imp is just there to help, then it’s perfectly fine. I would make sure to give the rogue the main part of this side quest, meaning both the bigger share of the difficulty and the more important role. Sneaking is much more his job than the warlock’s, so he should be the prominent one. [Suggestions: They need to steal something too heavy for the imp to lift, they need to pick a lock on the object, the direct area of the object is warded to detect fiends, etc.

How to Use – Combat Encounter 1 (difficulty 4)

The imp’s best combat strategy would be to sneak up while invisible on a PC not carrying a melee weapon, attack, and then run for cover that same turn. Next turn, he can turn invisible and change position [turning invisible only to stay in the place where they know he is being kind of stupid], and then repeat, attacking every other turn.

He does take an attack of opportunity when he retreats after attacking, which is why he attacks someone without a melee weapon. [He might accidently target a monk once, but not twice, and not if he sees them fight first.] If he can’t attack that PC without taking an opportunity attack from another PC as well upon retreating, he’ll wait until a good opportunity comes.

This is going to be extremely frustrating monster for your players to have to fight. Your players may try to deal with it by getting into position to take out the imp on the round he’s visible, after he retreats. If you don’t want the imp to be killed during this round, you’ll need to prepare a spot where he can hide, perhaps a crack in a wall or behind a bookcase. Make accessing the spot at least a little difficult. (High up, and/or behind something that the players can’t break or can’t afford to break is good.)  Taking out or gaining access to the spot will let the players win the encounter pretty quickly.

I would also give the imp have a special spot where he moves to on the turn he becomes invisible and therefore can’t attack. If you can add a high up spot at or near the center of the room where the imp can rest and have a good viewpoint over the room, that would give your players a useful clue. (The imp isn’t stupid, but he’s probably stupid enough to make the mistake of using the obvious spot. Also, to repeatedly use the same spot.)

If you are going to run this fight, I would prepare a few pieces of paper ready to hand out to players who successfully make perception checks to try to find the imp. On the paper it should also remind them that if they give away the location in an obvious manner, such as by saying it aloud or moving straight there, the imp will change locations. (Moving straight there won’t work according to D&D’s rules, but it should.)

I would prepare a few pieces of paper with just the reminder, on the grounds that the imp might follow them to a different room, and you’ll need to write out the location on the spot. Having the reminder ready to go will help speed things up.

Combat encounter 2 (difficulty varies)

A different way to use an imp in a combat encounter is if there is a lever or levers opening/shutting a portcullis, extending or dropping a bridge, moving walls around, raising/lowering platforms, or the like. You’ll need to run this encounter with a different enemy, a large amount of lower CR’s being preferable. Your players will have to fight the enemy with a strong chance that the imp will sneak behind them, dropping the portcullis to split their party at the wrong time, or raising it for the enemy to come in.

Having multiple levers in multiple spots will make it impossible for them to guard the levers. You can decide if you want it or not. I would have each lever do something different. Having several levers that do the same thing just to give the imp an opportunity feels like a cheat.

If you want to utilize the idea for all its worth, I would start with several small rooms [and/or areas inaccessible without the levers, such as bridges and raised platforms.] The players have to clear all, or a number of, the rooms. Without the imp, they would simply choose the order of the fights. With the imp, it will be more interesting.

You’ll want to make certain that only a certain number of levers are accessible at the beginning, with more becoming available as the players clear rooms, retrieve keys, or the like. If not, the imp can overwhelm them by opening all the levers at once.

Bargaining with the devil

The imp is probably the devil used most often to strike deals with mortals, in order to gain their souls. (At least I presume. I am amazed that there isn’t a single devil type built for this purpose.)

There are three types of bargains that the imp, [or other devil,] will try to strike.

The first is to bargain directly for the soul. I.e., the person’s soul belongs to the devil after death, and in exchange the devil will provide something. This type of bargain I would not make with the players. Hopefully they’ll refuse, in which case it will end there. [It is really not fair to pressure them into making a mistake. That is the very worst type of railroading, and the one that even the most tolerant player will dislike.]

You can have an NPC do this, however. I would suggest using it at the end of a plot line with a humanoid villain, particularly if the villain is a crime boss or a traitor. It will give him the reinforcements needed to provide a final, epic fight.

The second way is for the imp to bargain them into agreeing to do something that it doesn’t think they can do, so that it can collect their soul as penalty. The third way is for the imp to get them to agree to something that will mess them up. Either of these can be done with your players, but you need to make certain that they can come out ahead.

When building such a scenario, you generally want something that the players don’t know how it will be important. It should seem innocent, but at the same time there needs to be a plausible reason why the imp would ask for it. Ideas below:

Bargain 1: The imp challenges them, saying that it doesn’t believe they can defeat the dungeon, and that they’ll probably give up and leave in the middle. The trap is that they’ll need something that they can’t get in the dungeon.

If they’re betting their soul [see below], you’ll have to provide ways for them to win. Perhaps they can pay or manipulate an NPC into fetching it, perhaps they can obtain it through magical means, perhaps they can find a way around needing it. [You’ll want multiple ways, and you’ll want to be receptive to ideas your players come up with that you haven’t thought of.]

Bargain 2: The imp offers to reveal the location of the various potions around the dungeon, on condition that they don’t use any of the potions it tells them about while inside the dungeon. [To disguise its plan, perhaps have it offer this if they can win a minor bet, such as retrieve a certain treasure. It plans for them to win.]

Then it tells them about several potions that are in plain sight, and possibly about their own potions, thereby removing their usage within the dungeon. To complete the inconvenience, have an area of the dungeon that is difficult without the potion set there to assist them. [For example, a potion of fire resistance and a burning floor.]

Bargain 3: The imp asks them not to harm its master. In exchange, it’s master will agree not to attack them [the imp might provide other incentive to get them to agree.] Their master will utilize this to stand in the middle of the other enemies, thereby preventing area of effect spells. He can also buff and heal the enemies, and cast spells that aren’t directly onto the PCs. [For example: Turn Earth to Mud, in front of them or even in a ring around them.]

If all that was promised was that the imp’s master would agree not to attack them, he can agree and then promptly violate his word. If you do this, provide ways for the players to lock him up or otherwise restrain him.

Bargain 4: The imp strikes a bargain that they can each ask each other three questions, and they have to answer, and answer truthfully. [If it can be misleading, all the better.] It will wait to use its questions to trip them up when negotiating with NPCs [question: “What do you think of the NPCs?”], or by asking them about their path and then taking the opportunity to ensure that their answer becomes unwise for them.

[Examples: which room will you enter first. Then it can tell the other villains that the other rooms are safe to stand in and cast spells until the PCs enter the room in question. The PCs come to a place where they can choose one of three treasures. The imp askes them which one they are going to choose and then works to ensure that they can’t reach that one, or that it gets broken before they reach it.

Bargain 5: The imp gets them to agree to give it one treasure from the dungeon. Once they refuse to let it choose anything it wants, let them agree that the imp will choose two treasures and they’ll choose which of the two it gets. Have it choose two of the following: An item one of them really wants, an item that will be extremely hard to get [or even better, an item that removing it from its spot will place a curse [debuff] on them,] a needed quest item, and an item that the imp can use to unleash something dark onto the world [possibly by bringing it to an ally/master.]

Bargain 6: [Note: Can be used together with bargain 4.] The imp’s request is that they’ll do something small for it, or answer a question for it, at a time of its choosing. Until that is done, they can’t work directly against each other. This seems only logical, as otherwise they could kill the imp before it names its price.] The imp will wait until the perfect moment to betray them, and then demand its price. Once that’s given, it can immediately betray them. Done properly, they won’t even realize what happened until they paid the price, and the imp is betraying them.

In addition to literal betrayal, as in letting the villains know something that the players don’t want them to know, [such as the fact that the PCs are located here, right now,] there are also a few other ways the imp can act against the players. These include bringing down a portcullis to split them in two, pulling a lever to open a trapdoor or collapse a bridge under their feet, or activating a trap or set of traps right when the PCs are in a horrible position to survive it.

I would suggest ensuring that the players know that these dangers are there before the imp demands its side of the bargain. The best way to do that would be by having the players have already dealt with the obstacle in question.

They could have pulled the lever to open the portcullis or close the trapdoor in the first place. [Ideally, with the lever being behind a trap, or otherwise hard to access. Without that, they’ll either wonder why you placed a lever there and get suspicious, or they’ll state that they pull the lever as a matter of course, without really registering its presence.] With the trap, have them make their way past it before the imp pulls it on them.

(I’m only providing ideas for what the imp can demand from them. It’s up to you to decide what the imp offers in exchange. Information is always valuable, especially of the location of magic items or the like. He can also agree to avoid doing something that they won’t like, especially if there is a villain that he might have alerted or a portcullis that he could have brought down on them.)

In some of the ideas I suggested a wager. The stakes can be their soul, in which case you have to let them win. You can instead have the imp can demand a treasure, or an accomplishment that will be hard to accomplish in a moral manner. [Do not force your players to kill someone innocent. The imp might intend that, but provide a different way for them to meet the bargain.] This will make it possible to actually give the imp a chance to win.

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About Me

I have been a DM for several years, and I was designing home RPG games since my young childhood. I have been a fan of many different types of games (computer, board, RPG, and more) and have designed several for my own entertainment. This is my first attempt to produce game content for a wider audience.