• Justin Handlin

Puzzles, Predicaments, and Perplexities

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Puzzles for your Dungeons and Dragons games!

Adventurers will find themselves tested in many ways during their careers seeking fame, fortune, justice, and truth. Some of these tests will challenge their strength, agility, spellcasting knowledge, and combat skills. Other encounters will require diplomacy, conversation, observation skills, and social interaction. A rare challenge provides elements of both and requires deeper thinking and analysis. Such puzzles are meant to guard treasure and secrets, and present a unique challenge to characters and players. They also suggest a worthy reward lies on the other side.

Adventurers need much more than just brute force, magical powers, and nimble moves in order to survive the dangers that await them. A sharp mind is just as important as a sharp sword. When faced with a challenging puzzle, finding the solution can be the difference between victory and defeat.

Puzzles, Predicaments, and Perplexities II is the sequel to the best-selling original Puzzles, Predicaments, and Perplexities. This volume contains a collection of logic puzzles, brainteasers, and encoded sequences intended to test the problem-solving and deductive reasoning of characters and players, as well as two adventures that connect these puzzles with an overall storyline. These puzzles are designed to be easily placed into any adventure with no additional work, yet also provide guidance on how Dungeon Masters can customize the details to best fit into their own campaigns.

Inside you will find:

  • 15 original puzzles for use in your adventures.

  • 2 full-length adventures for characters of all levels that connect the included puzzles with an original story.

  • A new “Perplexity Rating” that provides guidance on the relative difficulty of each puzzle.

  • Instructions on how to scale the difficulty of the puzzles for characters of all levels.

  • Hints for each puzzle to guide players towards the solution without simply giving it away.

  • Guidance for customizing the puzzles to fit into your own adventure, campaign, or original world.

  • Optional “Raise The Stakes” sidebars for making puzzles more deadly.

  • 2 original maps suitable for in person or online play.

  • 8 original hand-outs that help visualize the layout, runes, and arrangements involved with some of the puzzles.

  • 4 unique magical items that can be found within the included puzzles and adventures.

  • 2 original creatures are confronted within the puzzles.

In this episode Crit Academy Covers:

Perplexity Rating and Scaling Puzzle Difficulty

The Skeleton Court

Three skeletons sit upon thrones facing the center of the room. Gemstones rest in their empty eye sockets. Before them are three small wooden chests on raised pedestals. The corpse of an unfortunate adventurer lies crumpled on the ground in the center of the room. Several arrows protrude from the body. The skeletons silently watch as events unfold before them, waiting to judge the actions of those who dare enter the chamber. Those who present the expected tributes will be rewarded. Those who fail will be punished.

Tales from the Crypt

A powerful magic golden scepter was buried in the crypt of the adventurers who retrieved it many years ago. A new threat requires the retrieval of this item. But the adventurers did not leave it unguarded. The party will have to gather clues and piece them together in order to solve the riddle of the crypt and prove themselves worthy of the legendary artifact.

To Tell the Truth

There has been a murder in a small town. Residents of the town swear they saw Boris, a local food vendor, near the scene of the crime. The local wizarding police set out and arrested Boris. The only issue is somehow they’ve arrested three versions of him. Clearly, two of them are murderous doppelgangers, and one of them is the innocent Boris. During the interrogation of the suspects, a rookie wizard’s truth spell malfunctioned. Now each Boris is stuck in a trance-like state and can only say one line, and only one of them is telling the truth. With the townspeople demanding justice, the wizarding police have no choice but to start the executions. Only fate can save the innocent Boris at this point. You are that fate.

Unearthed Tips and Tricks! We bring you new and creative content for you to bring with you on your next adventure

Character Concept: Book Smart Amazon

Rosari Utheraki is a fierce warrior with long purple hair dyed by the rare moxi flower that grows at the top of the island mountain range. She was born and raised on a floating island of warrior women known as Amazons. Their entire culture is based on strength before weakness. They believe that men are weak as they give into their emotions; anger, greed, jealousy. This weakness is why she despises most men.

Rosari was never the strongest of her sisters. While she has an athletic build, her gifts lie elsewhere from brute strength like many of the strongest Amazons. This often put her at odds growing up with her sisters, as they teased and laughed at her expense at her weakness.

While others spent their free time resting and fooling around, she continued her education beyond that which was required, leading her to become an expert marksman, as well as earning the ire of her Den Sisters for always outsmarting them and making them look a fool.

Monster Variant: Lackey

Lackeys are the weakest members in a band of bandits or small groups of crooks. They are weak and have little or no skills, but can be fiercely loyal to a powerful or charismatic leader. Though, once their leader is taken out, they are just as likely to run away as they are to try and gut you.

Origin: Noble

Replace breast plate with leather armor - 12 AC

Change rapier to short sword

Change parry to - Fight Dirty- Throwing dust in the enemies eyes,

Pact Tactics. The lackey has advantage on an attack roll against a creature if at least one of the lackey's allies is within 5 feet of the creature and the ally isn't incapacitated.

Encounter: Search Party

PC’s are hired to seek out a missing adventurer and recover them or evidence of their demise. During the investigation they not only do they learn the location of the adventurer, but evidence suggests that they are dead. But their corpse is nowhere to be found. They finally track down the corpse and find it impaled on spikes atop an oversized cadaver collector.

Magic Item: The Lost Lantern of Leonara (Puzzles, Predicaments, and Perplexities II)

Wondrous Item, legendary (requires attunement)

The lantern has 10 charges. While holding it, you can use an action to expend 1 or more of its charges to cast one of the following spells from it, using your spell save DC: light (1 charge), dancing lights (1 charge), branding smite (2 charges), guiding bolt (1 charge), dawn (5 charges), wall of light (5 charges), sunbeam (6 charges), or sunburst (8 charges). Undead targets have disadvantage on saving throws against these spells.

The lantern regains 1d6 + 4 expended charges daily at dawn. If you expend the last charge, roll a d20. On a 1, the lantern blackens, turns to dust, and is destroyed.

Dungeon Master Tip: Use magic spells for adventure and encounter designs.


Magic Jar allows a caster to lock their soul into a container until dispelled, while doing so they lose control of their own body, but can instead possess other humanoids within 100 feet, locking their soul inside. This could make for great shenanigans, trapping another players soul inside without the party knowing.

Guards and Wards effects a large area to cause foggy areas that confuses the directional senses of those trapped inside, auto filling stairs with webs that stitch themselves back together making it appear as nobody has passed through.

Magic Mouth and Programmed Illusion are also great as you can have canned responses based on a condition.

Player Tip: Don’t be a Dick Mark of your Pact!

When your warlock makes a pact with their patron, allow some residual effect to indicate the pact. Pact with a fiend may leave your eyes bloody, or your teeth charred black.

Pact made with archfey may cause flowers to bloom upon your passing, or small critters to be drawn to you. (like a Disney princess maybe).

Making a pact with a celestial may turn all water you bathe in, into blessed holy water, or into wine.

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