Dungeons & Dragons Online

A Big List of Challenges (Problems/Goals/Complications/Encounters) for your adventure (including Social, Exploration, Stealth, Mystery, and Combat).

Hi! I have compiled a big list of challenges your players can encounter during the adventure.

  • These challenges can be used as sub-goals the players will need to achieve on the path to their main goal, as obstacles they need to overcome to get what they want.
  • Most of them can also be used as the primary goal, an idea for the whole adventure (just make the stakes higher, make it important/interesting/exciting to accomplish, make it more difficult, add sub-goals and obstacles players need to get through to achieve it).
  • Challenges can be mixed and matched. In one adventure, challenge A can be the big primary goal, and challenge B can be a step towards accomplishing this big goal. In another adventure, it can be the other way around. In one adventure, the players need to obtain an item (a powerful weapon) to slay a monster, in another, they need to slay a monster to get their hands on the valuable item. In one adventure they need to rescue someone who has a clue to the mystery, in another they need to solve a mystery to be able to rescue someone.
  • Use multiple challenges together to add more depth, make the adventure more difficult/interesting, get players to fight on several fronts. Combine challenges to make them complications for each other, or use conflicting challenges that are incompatible with each other to create difficult choices. Players need to protect a person while also being on the run from the law, they need to spy on someone while traveling through the dangerous environment, they need to fight for political power while pretending to be someone they're not, they need to slay a big monster in the middle of the city while protecting people and avoiding collateral damage.

If you find this list useful – please help me to improve and extend it!

  • Share more challenge ideas, how can these challenge lists can be extended?
  • What other big challenge categories could I add? Please share a few challenge examples in those categories.
  • Share interesting examples for each kind of challenge.
  • Share interesting complications and combinations of challenges.
  • Share feedback/advice/ideas on improving this project.
  • Share good resources (books, random tables, articles) I can use to extend this list.


  • Defeat a villain and his minions.
  • Defeat a monster/creature/horde.
  • Obtain a McGuffin (item, vehicle, money, magic artifact, spell, etc)
  • Obtain Information.
  • Protect/Escort a person.
  • Deliver a person (make sure they don't escape).
  • Rescue a person/creature (rescue a hostage or a kidnapped person, break out of captivity)
  • Track, Find, Chase, and Capture/Catch a person/creature/vehicle (A criminal, a runaway, a ship, a lost pet).
  • Deliver a valuable/fragile item/cargo (protect it from danger).
  • Destroy the target (an object, enemy weapon or infrastructure, interrupt a ritual, the enemy base).
  • Sabotage a plan (disrupt a ritual, prevent a prophecy, undermine the invasion, prevent villain from achieving their goals).
  • Capture the base/location (enemy city, friendly city under siege, building, secure a military target).
  • Defend a location (protect a village from monsters, a city from the enemy army).
  • Your town/building/ship has been captured and overtaken by enemies.
  • Robbery/Heist (a person, a location, a vehicle).
  • Abduct a person.
  • Protect many innocent people.
  • Win a competition (Complications: your team is bad, the other side cheats, you can only win by cheating, the event is more deadly than it was supposed to be. You are competing for other purpose than victory, such as to keep another contestant safe, to spy on one, or to get into the place where the event goes down, to prevent villain from winning, to prove yourself, to impress someone).
  • Prepare for the mission. Get equipment/supplies/transportation/funding.
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  • Survive/avoid environmental dangers (think of the place itself as the “villain”, it is a monster without HP that "wants" to hurt players or drain their resources, and has certain powers to accomplish that. Traps, cave jns, lava eruptions, rockslides, etc).
  • Overcome environmental obstacles (abyss or river on your way, a closed gate).
  • Travel through multiple locations to reach a target.
  • Explore the location (to learn about it, to map it, to find something, to figure out what happened here).
  • Find a lost location/person/item/treasure/clues.
  • Scout for information, survey the location/region.
  • Clear location of danger (creatures, traps, haunting ghosts, curses, infestation)
  • Track something/someone, find a trail.
  • Deal with a natural disaster (storm, earthquake, flood, meteor).
  • Survival (without food/water, deal with harsh weather, diseases. Find shelter. Repair a ship or a radio. Find a way to get back home.)
  • Enter a guarded area (overcome defenses, defeat security, sneak in unseen)
  • Escape guarded location (break out of prison)


  • Convince/Persuade a person to do/say/give you what you want.
  • Intimidate/Manipulate/Blackmail/Force someone to do what you want.
  • Befriend/Seduce someone, make allies.
  • Find a non-combat resolution.

  • Persuade a group of people (an organization, an angry mob, nobles)

  • Gain social status, power, political influence (prove your worth, gain respect, impress someone, get elected).

  • Change someone's social status (make them look good/bad, get them elected, overthrow a ruler).

  • Run a kingdom/village/team/organization/business, lead an army (build a new one, restore the failing one to former glory).

  • Change society/group/organization (raise morale, lower the crime, stop witch hunts, deal with corruption).

  • Gain control over the territory (invade a country or repel the invasion).

  • Put down or incite rebellion/mutiny/conspiracy.

  • Negotiate a deal, bargain (political compromise, hostage negotiations).

  • Resolve conflict, broker peace, unite rivaling factions.

  • Establish political/trade relationships .

  • Navigate a strange culture/customs (without offending anyone)

  • Cause conflict/rivalry/war, pit people/factions against each other.

  • Deceive a person

  • Set someone up, shift the blame to someone else.

  • Infiltrate a group (conceal your identity)

  • Find the spy/traitor/mole.

  • Deal with being blackmailed, spied on, threatened, manipulated.

  • Find out if the person is lying or keeping secrets, and what they are.

  • Figure out someone's plot/motives.

  • Figure out who's behind the plot.

  • Interrogate

  • Defend someone (or yourself) in the court.

  • Prosecute/judge someone in the court.

  • Put on a show, entertain

  • Redeem or corrupt a person (teach someone a lesson).

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  • Spying/Surveillance (gather information on a person, a location, a wild beast. Without being noticed. Follow them.)
  • Steal (or plant) an item/information.
  • Escape from danger (overwhelming force, ambush, pursuit of the law or criminals).
  • Hide, cover your tracks, lay low.
  • Sneak through undetected.
  • Assassinate stealthily.


  • Investigate/Solve a mystery (interview witnesses, find clues and put them together to reach a conclusion)
  • Figure out what's going on, unravel a plot.
  • Figure out what happened in this location.
  • Find evidence (proof of innocence or guilt, expose a corrupt official)


  • Do it under time pressure (before the ritual is complete, before people run out of air, before or during the event, in transit, while you still hve the chance).
  • Do it while competing with a rival team.
  • Do it stealthily.
  • Do it while pretending to be someone else.
  • Prevent collateral damage, protect the innnocents who are around.
  • Avoid violence. Defeat/capture the villain/creature without it being harmed.
  • Mirigate the risk, there's a high probability of causing a lot of damage if you're not careful.

  • Two challenges conflict with each other (you must break your stealth to help someone in trouble).

  • Difficult choice. Choose lesser of two evils, choose which people to rescue. A goal requires personal sacrifice.

  • Resolve moral dilemma (the creature is dangerous but doesn't deserve to die, you're working for a bad guy, both sides of the conflict have valid points).

  • Do it with incomplete information.

  • Do it with limited resources or without preparation.

  • Do it without access to powers you're used to having (while sick/injured/debilitated, in an area where magic is outlawed/disabled, having lost your equipment).

  • Locals here are unhelpful/hostile to you. You have low social status.

  • You can't trust anyone.

  • Doing it is illegal, or against authorities best interests, threatening a powerful group.

  • There are regulations/restrictions on what you can do.

  • Do it while being supervised (the media is all over you, a brilliant detective is on your tail, you are under suspicion, the enemy knows you're coming, you have a spy/mole).

  • Do it despite your flaws/temptations/fears.

  • It causes conflict/infighting within the team (player characters will have opposite goals/reactions to it)

  • Do it while working together with antagonist or someone else you don't like.

  • The side you're working for turns out to be evil.

  • The villain is someone you know/like/respect.

  • The villain is a respected public figure, celebrity, is liked by people or has authority over you.

  • Bad guy has a dead man switch, if he dies others will suffer or treasure will be lost. Bad guy is the only one who knows the valuable information.

  • The people you're helping don't want your help.

  • Vital information turns out to be wrong.

  • Deal with betrayal.

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Please leave a comment and contribute to this project!

Source: reddit.com

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