The best tales climax when the heroes must choose between what they’ve learned is right and an easy route to what they thought they wanted. In fiction, such moral dilemmas reveal character. When a woman who only ever wanted to be queen realizes that someone else is better suited to the throne, will she still take the crown?

Everyone who enjoys games such as Dungeons & Dragons likes making choices and seeing the outcomes. Many of those players also enjoy exploring and revealing their characters. So in roleplaying, moral problems may rank as the most interesting and most revealing. In the Dungeon magazine article, “Temptations and Dilemmas,” printed in issue 148, Wolfgang Baur writes about the joy of posing dilemmas. “They make the player really engage with their characters and the game world. Sweet sweet perfection: all you have to do is let the PCs wrangle about it for a while.”

Creating moral choices in D&D proves harder than creating similar dilemmas in stories. In fiction, moral choices often force characters to pick between what’s right and what’s easy. But D&D characters rarely make decisions alone. They face choices as a party, and these groups inevitably mix rogues and paladins.

More than popular classes, rogues and paladins represent two ways players often imagine their characters’ moral outlooks. These make popular character perspectives because they bring escapes from either the restrictions or the unfairness of modern life.

In our world, we often feel bound by rules and obligations. Playing a rogue who’s free from ethical burdens and who boasts the power to ignore rules feels exhilarating.

In our world, we see misdeeds rewarded, good people suffer, and too often we feel helpless to act. Playing a paladin with the strength to punish wrongdoers, help the deserving, and right wrongs feels rejuvenating.

Choices between right and easy inevitably split a party’s rogues and paladins.

“Assassins, poisoners, sneak thieves, death priests, drug smugglers, necromancers, diabolists, and warlocks make it tough for more heroic, lawful, or good characters to look away or condone their smuggling, sneaking, theft, magical abuses, and so on,” Wolfgang writes. “There’s a dilemma for the party every time a character crosses the line and does something that another, more moral character might find unforgivable.”

In D&D, rogues and paladins must find ways to work together or the game falls apart. “If you wind up with that one paladin singled out and forced to choose to compromise his character just to keep playing, you have a problem.” See A Roleplaying Game Player’s Obligation.

So in D&D, moral dilemmas must avoid posing an unsavory-but-easy solution as an option. Instead these problems must force players to weigh which of two, imperfect choices brings the most benefit—or the least corruption. In “5 Tips on How to Design Diabolical Dilemmas,” Johnn Four imagines starting the party with a simple job to capture a war criminal, and then adds moral complications. What if the players discover that the elderly criminal now repents by running an orphanage? If the players decide to take him to justice, what if they learn that the alleged crimes may have saved a village? Do the players still bring the man to execution? None of these choices make the adventure easier for players, but they all land the players in thorny dilemmas that reveal characters.

Johnn suggests developing moral dilemmas by starting with a simple choice and asking questions that help you imagine complications.

• Who gets hurt?
• Who escapes justice?
• Who undeservedly benefits?

While moral dilemmas benefit the game, you can press too hard to create them. Players enjoy difficult choices in balance with uncomplicated situations where their power lets the good guys win. Often players use their ingenuity to solve a moral dilemma without any tough choices. Players savor those victories.

Even when DMs work to foster moral dilemmas, most D&D games only occasionally feature such situations. But one sort of quandary appears frequently, and it’s awful.

Blame co-creator Gary Gygax and his adventure The Keep on the Borderlands (1979). D&D’s first Basic Set included this adventure, so through the 80s, the keep easily ranked as the game’s most played scenario. In a reprint, D&D creative director Mike Mearls writes, “In its 32 pages, Keep on the Borderlands provides the clearest, most concise definition of D&D that you can find.” The keep showed countless dungeon masters how to create a D&D adventure, and mostly it set a good example.

What awful moral dilemma appears 8 times in this classic?

When Gary wrote the keep, he aimed to create an infestation of D&D’s various evil humanoids: kobolds, orcs, hobgoblins, gnolls, and lizard men. Gary favored applying some natural order to his imaginary world, which included various young monsters incapable of fighting.

After slaughtering the orcs’ parents, do you put their infants to the sword? As a player who favored the paladin type, I wanted to right wrongs, not debate whether to murder young. The rogue-types in the party would open the 1977 Monster Manual and point to the word “evil” beside a pig-faced monster, but I had no taste for the baby-orc dilemma. I want to smite evildoers, not kill helpless foes. I’m far from alone in that sentiment. Worse, young non-combatants appear in 8 of the keep’s locations, and then in the countless adventures that follow the keep’s example.

I recommend contriving situations that leave helpless foes out of reach. Instead of populating the Caves of Chaos with generations of humanoids, why not imagine war parties locked in a standoff?

Even though the baby-orc problem rates as something to avoid, other dilemmas can enrich the game. M.T. Black’s adventure The Lich Queen’s Begotten ends with an interesting variant on the question of whether to kill an innocent destined for evil. Both times I ran this adventure, a party of mixed paladin and rogue types chose to protect the innocent—not necessarily the easier choice. Both groups wanted a follow up adventure where they worked to thwart the innocent creature’s evil destiny.

That’s the sort of choice that makes heroes.