Encounter of the Week: Devil in the Details

This week’s encounter is titled Devil in the Details, and continues the loosely connected “road trip” encounter series known as On the Road to Baldur’s Gate. In this series, a group of adventurers will travel down the Sword Coast for nearly two months over road and wilderness, from the gates of Waterdeep to the threshold of Baldur’s Gate. You may use this series as an introduction to the upcoming D&D storyline Baldur’s Gate: Descent into Avernus, as an expansion to the caravan sequence in the first D&D storyline adventure, Hoard of the Dragon Queen, or piecemeal as standalone encounters.

You can keep track of this journey on this massive map of the Sword Coast, originally presented in the Sword Coast Adventurer’s Guide. The trip from Waterdeep to Baldur’s Gate covers about 750 miles of both road and off-road wilderness. A small party on horseback can cover about 24 miles per day at a casual pace, with just under two days off for rest per tenday of travel. All in all, this journey takes about a 45 days to complete for a small party of adventurers—assuming they’re well-prepared and no serious complications arise. And note, not every day of travel needs to be represented by an encounter; the characters may go for days with only minor encounters with passing merchants or travelers.

This is the second encounter along this journey. The first is The Road to Baldur’s Gate.

Social Encounter: Devil in the Details

This social encounter can lead to benign benefits or malign misfortune, but likely won’t become dangerous unless the characters attack their benefactor. If they come to blows, this combat is suitable for characters of 1st level.

This encounter involves a deal with a minor devil—an imp named Pip Kip, to be precise. This imp happens to be on a journey as well; it’s stranded on the Material Plane after its summoner was killed, and is living the high life by preying upon travelers, all while slowly and meanderingly searching for a way to return to the Nine Hells without being killed first. The imp hopes that, by consigning a few souls to the Nine Hells before returning, it will be promoted on its return. Pip Kip prefers to travel invisibly and accost mortals in its raven form, which the imp considers the most regal and refined of its beast forms.

When Pip Kip meets the characters, the imp offers them a chance to gain great wealth and power by signing contracts. The imp’s contracts are tricky and full of nasty, contradictory clauses that could cause a character to violate the terms of the contract without even knowing that they had done so. And when it comes to the devils of the Nine Hells, breaking a contract has only one penalty. A fine. A simple fine, really: your soul. Any being that breaks a contract owes their soul to the archduke who rules over the contract’s drafter, payable immediately upon the signer’s death. This imp is a sworn lackey of a spined devil known as Rakkathrax, and that spined devil serves a bearded devil, up and up to the zenith of this hierarchy: the archduchess of Avernus, Zariel.

Pip Kip isn’t particularly clever, so its contracts aren’t as treacherous as those drafted by brighter devils, but they still have the power to ensnare a foolish character. A character that reads a contract carefully can make a DC 15 Intelligence (Investigation) check after 10 minutes of careful study. A character that can read Infernal has advantage on this check. Pip Kip hates when people read its contracts too closely, and badgers and harangues the character in an attempt to get them to stop reading. On a success, the character identifies a tricky clause in Pip Kip’s contract. If the character succeeds on a DC 13 Charisma (Intimidation) check, the character can cow Pip Kip into removing the clause, otherwise the imp simply shrugs and says, “No deal, then,” and the contract vanishes in a sulfurous cloud.  

To determine a contract’s benefit, its price, and its trick, roll once on the table below. If one character is offered a deal that appeals to anyone else, another character can ask for the same deal. If a character is in possession of a soul coin, such as the one they could have acquired in The Road to Baldur’s Gate, they can use it instead of the contract’s stated cost—or in place of their own soul, if they break their contract.




Devilish Trick


For the next 10 days, whenever you touch a silver or copper coin, a duplicate coin appears next to it in a cloud of sulfur. This boon doesn’t affect coins already in your possession, or coins that have already been duplicated, or their duplicates.

10 gp and one of your fingerprints

If you duplicate coins that belong to someone else, even with their consent, the contract is broken, and all duplicated coins turn to ash.


For the next 10 days, you sleep with incredible soundness. Whenever you complete a long rest during this time, you gain 10 temporary hit points which last until you complete another long rest.

Four hours of restful sleep to be paid from subsequent short and long rests, and all your eyelashes

If you sleep during sunlight hours for any reason, the contract is broken and you suffer from nightmares for the next 10 days.


For the next 10 days, your pack will always have enough food to eat and wine to drink, and it tastes better than any food or drink you’ve had before. On a day when you eat this magical meal, you are immune to poison damage and the poisoned condition.

All of the food in your possession, and a vial of your saliva

If anyone other than you eats this magical food, the contract is broken and all food you eat tastes of ash for the next 10 days.


For the next 10 days, your gear feels as though it weighs nothing at all, and you feel as though you could walk day in and day out. During this time, your carrying capacity is tripled, and you are immune to exhaustion.

20 pounds of your own equipment, and a vial of your sweat

If you carry any creature, or items that belong to someone other than yourself, the contract is broken; you gain 1 level of exhaustion and your carrying capacity is halved for the next 10 days.


For the next 10 days, you are blessed with a good mood and a courageous heart, and all who speak with you are cheered by your presence. During this time, you are immune to fear, and can cast charm person at will, with a save DC equal to your spell save DC or 8 + your proficiency bonus + your Charisma modifier, whichever is higher.

An article of your own clothing, and a vial of your blood

If you force any humanoid creature to do something against its will, the contract is broken and humanoids and beasts instinctively mistrust you for the next 10 days, imposing disadvantage on all Charisma checks you make to influence them.


For the next 10 days, temperature and weather have no adverse effects on you; you are constantly comfortable. During this time, you are resistant to cold, fire, and lightning damage, and the effects of extreme weather.

Any hot- or cold-weather clothing and torches, lamps, and fire-making tools in your possession

If your body is completely immersed in flame, ice, freezing water, or struck by lightning, the contract is broken and you gain vulnerability to cold, fire, and lightning damage for 10 days.

Encounter Summary

While traveling south along the Trade Way, the characters meet an imp named Pip Kip, in disguise as a raven. The raven talks with them for a time, and eventually offers them a deal to make their travels easier. The bird encourages everyone present to take one of its deals, saying that these contracts will surely make their journey easier.

Encounter Start

The characters are traveling down the Trade Way. Just before highsun, read or paraphrase the following:

The sun climbs high into the cloudless blue sky, and the highsun heat beats down upon you in waves. To one side of you is a small copse of trees, and to the other are the distant, sapphire waters of the Sea of Swords.

A bird flutters from a nearby tree, casting a tiny shadow beneath it as it circles around through the air. It seems to stay near you as you ride down the road, and eventually it alights upon a crumbling stone wall on the west side of the road. This raven cocks its head at you and says, “Oi, you! You look like a damned sweaty traveler. Come over and let me help you out.”

This raven is actually an imp named Pip Kip, and this lesser devil is hoping to scam some unsuspecting mortals out of their souls while stranded on the Material Plane. Pip is a brazen braggart and a sly salesman, but all of these traits are trumped by its cowardice, and it prefers to keep its fiendish nature hidden for as long as possible, choosing to remain in raven form unless it thinks it can gain something out of revealing its true form.

Once the raven has been properly introduced to the characters, it offers to make a deal with the travelers—individually, of course—that might make them more comfortable on their journey. If any of the characters express interest, Pip Kip chooses one of them and a long scroll appears in the raven’s beak in a plume of sulfurous smoke, and unrolls down to the character’s feet. The raven gives the character a few moments to deliberate, but loses its patience quickly and starts haranguing the character to make a decision. “You want to ensure your safety and comfort on this journey, don’t you?” it snaps. “Listen, I’ll sign first if that makes you more comfortable!”

If Pip Kip is in raven form, it steps on the contract with a raven foot—producing an Infernal signature that hisses and steams as if impressed with a branding iron. When a character signs one of Pip Kip’s contracts, the parchment instantly rolls tight and flies into the imp’s mouth, which it swallows. For more information about Pip Kip’s contracts, see the beginning of this encounter.

If the characters attack Pip Kip, it turns invisible as soon as possible and flees. After it completes a short rest and recovers its hit points, it flies down the road in hopes of finding the party and launching a surprise attack.  


If even one of the characters signed a contract, Pip Kip considers the morning a success, and flies off with a squawk. If no one signed, the imp lingers, fuming, for a few hours. It follows the characters and continually bothers them, demanding that they make a deal and save themselves a lot of heartache on the journey. If they still refuse, Pip Kip furiously turns invisible with a tiny popping noise and follows the characters for the next ten days. If any of the characters come to serious harm in this time, Pip Kip swoops down and whispers in their ear, offering to save them in exchange for their soul—but only after they die, of course.

Over this time, Pip Kip may even develop a fondness for one or more of the characters, and may become the familiar of a wizard or a warlock, or even just decide to hang around because the imp likes their company.

Are you excited for Baldur's Gate: Descent into Avernus? It's available for pre-order now on the D&D Beyond Marketplace!

Did you like this encounter? If you want to read more adventures, take a look at the other encounters in the Encounter of the Week series! If you're looking for full adventures instead of short encounters, you can pick up the adventures I've written on the DMs Guild, such as The Temple of Shattered Minds, a suspenseful eldritch mystery with a mind flayer villain (for 3rd level characters). My most recent adventures are included in the Gold Best Seller Tactical Maps: Adventure Atlas, a collection of 88 unique encounters created by the Guild Adepts, which can be paired with the beautiful tactical poster maps in Tactical Maps Reincarnated, recently published by Wizards of the Coast.

James Haeck is the lead writer for D&D Beyond, the co-author of  Waterdeep: Dragon Heist and the Critical Role Tal'Dorei Campaign Setting, the DM of  Worlds Apartand a freelance writer for Wizards of the Coast, the D&D Adventurers League, and Kobold Press. He lives in Seattle, Washington with his partner Hannah and their feline adventurers Mei and Marzipan. You can usually find him wasting time on Twitter at @jamesjhaeck.


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