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Writer's pictureJustin Handlin

7 Tips on How to Craft Dastardly Plots in Dungeons & Dragons


“Bring on the railway track with the bound captive, the mustache to twirl, and the scheme to endanger the World As We Know It.”

-Ed Greenwood-


Heroes and Plots

What is the difference between an adventurer and a soldier? The answer is simple, one seeks out to change or influence the world in some fashion. The other just takes commands and lets others decide what is best. Regardless if the PCs seek to be heroes or tyrants, they seek to be agents of change. A change they hope to steer to their desired change.


Enter plot or in other words the outline or script of the story, often a book, movie, or similar medium. Depending on the skill of the writer and forethought placed into it, maybe convoluted or it may be festooned with diversion and subplots within. In the end, there is generally an overarching “plot”.


Unlike a novel or movie where the goal is to entertain, but there is only one writer who lays out the plot and string events, roleplaying plots get to not only choose the events to engage in, they can alter it significantly. Shaping the unfolding story is the core of Dungeons & Dragons.


There is much satisfaction in slaying monsters, looting treasure, and discovering secret lore and locations. But these can often be forgettable. What makes for memorable moments and lasting satisfaction in roleplaying is when the players feel their characters have achieved something meaningful, when their actions change the world in some small way. That is why it is critical when designing your D&D stories and campaigns to ensure that the plots must be flexible. Keeping this hidden from the players lets them feel as if their characters are uncovering the plot, not them.


What is a Dastardly Plot?

So “what the villains are up to” make up the “dastardly plots” that provide resistance to PCs in most fantasy roleplaying campaigns, forcing them into adventures, and are the plots that concern us there.


Pretty much any scheme hatched by a villain, no matter how big or small that is designed to help prevent the characters from potentially stumbling into, or stopping the same villain’s scheme that is underway is considered a “dastardly plot” according to Ed Greenwood.


Smaller plots that link to much larger plots tend to last longer and have much more influence on the gameplay as a whole. Because they are layered, the plots become interconnected and require the heroes to spend more time uncovering each strand to understand how they are connected. Defining what a dastardly plot is, is just the start. We want to talk about what makes a plot juicy and memorable, what makes the story thrilling and exciting to be a part of, and drive the story forward to uncover the secret. Keep in mind, this doesn’t simply apply to the DM, characters can have their own plots as well. They enjoy scheming and politicking as much as the DM. This means we need to ensure each plot or story point is somehow connected to the dastardly plot.


7 Tips on How to Craft Dastardly Plots in Dungeons & Dragons

Dastardly Plots...

  • must contain both mystery and menace.

  • must contain surprise or attempt to mislead.

  • shouldn’t be easily figured out. They should require extensive investigation and/or exploration.

  • must have at least 2-3 contingencies in place.

  • should always include - obvious or not - some conspirators whose identity or whereabouts are unknown.

  • tie in flaws, bonds, or ideals of one or more of the characters.

  • often include betrayal.



Character Concept: The Seducer

I assure you my reputation is exaggerated—at least a little. But my reputation had to have piqued your curiosity, or you wouldn’t be here, would you?


You can’t keep away from romantic liaisons with the attractive and the alluring or with those who relate to a particular fetish. And after practice, you’re good at it, having slept your way through a dozen manor-houses and noble villas. How mercenary are your seductions—do you genuinely fall in love easily, or is there always an ulterior motive? Are you motivated by the sheer beauty of your paramours, the chase and conquest, or the fringe benefits of bedding the wealthy and influential? Is there someone who got away, or someone unusually resistant to your charms?


D&D Monster Variant: Tainted Treant

Origin: Young Black Dragon

Lost Features: Fly, swim, claw, bite, loses one of its multiattacks (down to 2)


New Features:

Tainted Aura. The treant gives toxic spores. A living creature that enters for the first time or ends its turn within 10 feet of the treant must succeed on a DC 14 Constitution saving throw or take 7 (2d6) acid damage on a failed save, or half as much damage on a successful one.


Vine Whip. Melee Weapon Attack: +7 to hit, reach 15 ft., one target. Hit: 15 (2d10 +4) slashing damage plus 4 (1d8) acid damage. If the target is a creature, it must succeed on a DC 14 Constitution saving throw or become diseased. The target's flesh begins to harden into a rough blackened tree bark and their legs begin to sprout roots. The target’s AC can’t be less than 16, regardless of what kind of armor it is wearing. The target's speed is reduced by 10 feet every round until it reaches 0. Additionally, the target becomes vulnerable to acid damage.


D&D Encounter: Irregular Business at Rose Keep

The characters are approached by one Lalita Laylodan, a noble mage whose family sits on the governing council of the city. Lalita indicates she wishes to employ the adventuring party as spies. She believes the Red Wizards of the enclave are in cahoots with local thieving guilds, and she thinks they are acting as a fence by reselling their ill-gotten gains as if it were merchandise purchased from other enclaves along the coast.


In truth Lalita has no such belief—she secretly wants to send the characters into Rose Enclave to, at minimum, disrupts the business operations of Rose Keep, or better yet, eliminate one more of the Red Wizards; adventurers are wont to swing swords first and ask questions afterward, in Lalita’s experience. House Laylodan secretly backs a black-market slavering, and according to her contacts, the Red Wizard named Dorin Dawnbringer, an archmage has been making inquiries into the business. She’d rather avoid the competition without making it appear as if she has anything to do with the matter, and even if it does come to everyone’s attention that she sent the characters into Rose Keep, well, she did so only because she thought the enclave concealed a fence.


D&D Magic Item: Barbed Displacement Whip of Mastery (Forged with Witiker’s Well of Wondrous Magic Items)

Weapon (Whip), Very Rare (requires attunement)


This whip was crafted from the tendrils of a creature that could craft an illusion to displace its location. Giving the appearance as if it was standing in a different location. A creature attuned to this weapon gains the following benefits:


When you roll a 1 on a damage die for an attack you make with this weapon you can reroll the die and must use the new roll even if the new roll is a 1.


When an enemy hits you with a weapon attack as a reaction you can speak this weapon’s command word. If you do, the weapon projects an illusion that makes you appear to be standing in a place near your actual location causing any creature to have disadvantage on attack rolls against you. If you take damage this effect ceases to function. This property can't be used again until you finish a short or long rest.


Speak this item’s command word and harness its hidden potential You can make a single weapon attack as a bonus action on each of your turns for 1 minute. You can't use this feature again until the next dawn


D&D Dungeon Master Tip: The Nobility - Lords, Ladys and Heralds

Nobles are born, not made. The exceptions to this are local lords and heralds, who are individuals appointed by a king or queen to govern a town or group of towns in the ruler’s name. Upon selecting a local lord, the ruler grants that person a noble title (if she or he does not already hold one).


Each lord defends the local farms, dispenses the King/Queens’s justice, keeps the peace, serves as “the King/Queen’s eyes and ears,” and collects tithes for the king/queen and for him or herself. Each lord or lady must have someone who serves as a clerk/record-keeper and is a trained herald.


The relationship between the landed nobility and the appointed local lords is good, though many established families treat local servants of the crown as no more than royal lackeys to be bossed about or flattered as need be.

-Dragon Magazine 365-


D&D Player Tip: Don’t be a Dick Knowing When to Fight: The Art of War for D&D Players

You will win if you know when to fight and when not to fight. . . . If you know the enemy and know yourself, you need not fear the result of a hundred battles.

-Sun Tzu-

Almost every monster you meet while on an adventure is dangerous, but not all of them are hostile. A lot of creatures in an adventure environment attack on sight, so when something doesn’t attack, it is worth keeping your sword in your sheath for a few moments while you try and start a conversation.


Why would you want to talk to a monster? Well, there are a lot of things a friendly or neutral monster may be able to tell you about an adventuring environment, such as:


• The location of any boss monsters

• The history of the local area

• The location of any prisoners

• The identity of an important enemy

• Information about disarming or avoiding a trap

• Instructions to open a secret door

• The weakness of a powerful monster

• How to get to the next level





Witiker's Wondrous Well imbues mundane items with powerful magic. Inside you will find three generators for magic items. These can be used to spice up any game as instantly generated loot or to diversify the weapons of enemies. Within, are weapons with incredible effects such as immolating the flesh of foes that their steel bites into, or simpler ones that emit light in dark times. One may also find armors that can withstand the toxic corrosiveness of a dark dragon or the frigid cold of an ice mage. Finally, there lie potions that can still the mind of the drinker and solidify their inner walls to prevent prying charms or spells from peeking or interfering within. Use this book for it all; it is here to serve you.

Winner: Greenbaychampion1

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