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This page is about the adventure. For the character, see Problem Sleuth (character).

Problem Sleuth is the third MS Paint Adventure. A parody of detective noir stories initially, the story quickly abandoned that premise in favor of stranger and wackier plot directions. It is an adventure that tells the story of Problem Sleuth, Ace Dick and Pickle Inspector, three competing private detectives who operate out of neighboring offices in the same building. When all three become trapped inside their respective offices, they join forces to find a way out of their predicament and defeat the evil Mobster Kingpin, who possesses the key they need to leave their building.

Problem Sleuth debuted on March 10, 2008, relaunching MS Paint Adventures after the abandonment of Bard Quest eight months earlier caused the site to be shut down indefinitely. Exactly one year later, on March 10, 2009, the central storyline reached its conclusion, and, after the release of an additional epilogue chapter, Problem Sleuth ended on April 7 with a total of 1,673 pages.

Numerical data about Problem Sleuth are maintained here.


Adv problemsleuth

The old Problem Sleuth logo


  • CHAPTER 1 - COMPENSATION, ADEQUATE (Started 03/10/08, ended 03/17/08)
  • CHAPTER 2 - TOO HOT TO HANDLE (Started 03/17/08, ended 04/06/08)
  • CHAPTER 3 - PERSECUTED BY UNSCRUPULOUS WHORES (Started 04/06/08, ended 04/14/08)
  • CHAPTER 4 - HAIRPIN TRIGGER (Started 04/14/08, ended 05/16/08)
  • CHAPTER 5 - THE DEGENERATE GAMBLERS (Started 05/16/08, ended 06/04/08)


  • CHAPTER 6 - MORE WEIRD PUZZLE SHIT (Started 06/04/08, ended 06/18/08)
  • CHAPTER 7 - FIT OF HYSTERICS (Started 06/18/08, ended 07/12/08)
  • CHAPTER 8 - THE SLEAZY BROTHEL IN THE SKY (Started 07/12/08, ended 07/30/08)
  • CHAPTER 9 - THIS IS COMPLETE BULLSHIT (Started 08/13/08, ended 08/19/08)


  • CHAPTER 10 - THAT WOULD HAVE BEEN SO BADASS (Started 08/19/08, ended 09/01/08)
  • CHAPTER 11 - TWO LUMPS (Started 09/01/08, ended 09/15/08)
  • CHAPTER 12 - SUITOR TO THE SODAJERK'S CONFIDANTE (Started 09/17/08, ended 09/26/08)
  • CHAPTER 13 - DMK (Started 09/26/08, ended 10/09/08)


  • CHAPTER 14 - ACTUALLY, THIS IS A LOT OF FUN (Started 10/09/08, ended 10/27/08)
  • CHAPTER 15 - TRIPLE COMB RAVE (Started 10/28/08, ended 11/02/08)
  • CHAPTER 16 - SUPERNATURAL GOURD (Started 11/02/08, ended 11/26/08)
  • CHAPTER 17 - BLACK LIQUID SORROW (Started 11/26/08, ended 12/11/08)


  • CHAPTER 18 - SUPERSTRING STRATA (Started 12/11/08, ended 12/21/08)
  • CHAPTER 19 - ASCENSION/ALIGNMENT/CONJUGATION (Started 12/21/08, ended 01/08/09)
  • CHAPTER 20 - TEMPORAL REPLICOLLISION (Started 01/16/09, ended 01/29/09)
  • CHAPTER 21 - BHMK (Started 01/29/09, ended 02/15/09)
  • CHAPTER 22 - SEPULCHRITUDE (Started 02/15/09, ended 03/10/09)

EPILOGUE (Started 03/16/09, ended 04/07/09)


Volume 1[]

One evening, Problem Sleuth (PS) prepares to leave his office and find some new cases when he discovers that the door will not open, trapping him inside. He begins to tear the room apart searching for useful items, like his gun and pieces of candy corn, and in the process, he comes into contact with Ace Dick (AD) and Pickle Inspector (PI). PI is also trapped in his office, and AD soon ends up in the same situation, so the three decide to abandon their rivalry and work together to escape, becoming Team Sleuth.

Searching the offices reveals that each detective's office contains hidden passages leading to other rooms in the building; PS's office is connected to a hideout and a jazz room, AD's is connected to another hideout and a room with stills for making liquor and hot sauce, and PI's links to an elevator and an elf room, both of which contain elves. These other rooms, in turn, all connect to one central room: a speakeasy operated by Mobster Kingpin (MK).

In parallel with their real-world escape efforts, the trio discover the existence of an imaginary universe accessible through one of two methods: getting drunk and playing make-believe inside a makeshift fort, which creates an imaginary body for the detective to control in the other world, or physically entering the realm by climbing through their offices' electricity-powered portal "windows." In this world, they explore an imaginary recreation of their city and do battle with loathsome beasts.

Eventually, AD's attempt to brew candy corn liquor in the still room causes an explosion that blows out his office's front wall, allowing him to exit it. He still cannot leave the building itself, however, because the exit door is locked and can only be opened with the legendary Megaton Key, currently in the possession of MK.

Volume 2[]

Before making much progress towards confronting MK, Team Sleuth is drawn into a conflict raging between four kingdoms in the imaginary universe. Each detective is conscripted by one of the factions to serve as their agent, with PS joining the elves, AD aiding the hogs, and PI assisting the weasels. Upon joining their faction, each detective is sent to the imaginary universe to complete a mission in one of the opposing kingdoms; upon successful completion of the assignment, the detective is rewarded with the opportunity to go on a quest of the spirit and gain awareness of his Female Alter Ego.

Each detective has a female counterpart that lives inside a dollhouse in MK's office: PS's is Hysterical Dame (HD), PI's is Nervous Broad (NB), and AD's, since he lacks the imagination needed to think up a female counterpart, is an identical male duplicate of himself. The three alter egos attempt to escape the dollhouse and enlarge themselves to full human size by exploiting the size-altering properties of portals between the real and imaginary universes.

Meanwhile, the members of Team Sleuth awaken in a new section of the office building, where their faction loyalties allow them to access new rooms. One of these rooms is a control room that allows alternate save states of Problem Sleuth to be loaded; the detectives use the controls to alter reality by allowing AD to skip an impossible puzzle and creating a third version of AD. Another is a lounge, where PI consumes some of the candy corn liquor and gains extraordinary imaginary power. He uses his power to create a number of duplicates of himself, including one that pilots a Candy Mecha, one who ascends to godhood and becomes Godhead Pickle Inspector (GPI), and one that splits into time-traveling counterparts, with one that goes to the past (to solve a puzzle for AD) and one that goes to the future.

PS is recruited by the Weasel King to draft a treaty that will end the war of the four kingdoms, revealed to have been started by the clowns and their agent, MK. When his diplomatic skill proves inadequate for the task, he uses a cheat code he finds in a GameFAQs walkthrough of Problem Sleuth to skip the treaty-writing and successfully end the war. Its work with the four kingdoms completed, Team Sleuth returns its attention to MK, who is in his office fighting the now full-sized female alter egos.

Volume 3[]

To reach MK's office, PS and two of the ADs must make their way up the five floors of the Cathedral of Syndetic Ascension and fight the thugs and beasts on each level. During the battle, the two ADs undergo physical transformations; one is bitten by a zombie and becomes Zombie Ace Dick (ZAD), while the other returns to the still room to make and consume 5 alarm hot sauce, turning into the super-strong Fiesta Ace Dick (FAD).

In MK's office, MK is able to defeat the alter egos by killing the "female" AD (who, due to the transformations of the other versions of him, is now the "regular" AD), defenestrating NB and knocking out HD. Simultaneously, PI is killed when he inserts a window into another window and causes a critical fractal reaction. The two slain detectives appear in the afterlife and challenge Death for the right to come back to life.

PS and the ADs make it to MK's office and discover that their nemesis has built and entered a fort, preventing them from attacking him. They exit the office and reach the deck of MK's flying pirate ship, the Chicago Overcoat, where they witness MK's imaginary self ascend/descend into demon-hood and become his hideous ultimate form, Demonhead Mobster Kingpin (DMK). The final battle begins between Team Sleuth and DMK, and the detectives receive reinforcements in the form of AD and PI, who have returned to the world of the living after beating Death, and PI's future-traveling duplicate.

In the first of his three forms, DMK's only weakness is his diabetes; he becomes more vulnerable to damage the more his blood sugar level is raised. He preemptively counters this by donning a metal mask, preventing Team Sleuth from force-feeding him candy, but the detectives overcome this obstacle by sacrificing their guns - which, due to a strange gameplay quirk, turn into keys - to unlock the mask. Meanwhile, HD and NB end up on the floating Whore Island, home to a sleazy brothel in the sky and PI's electric fan, which was enlarged and sent to the imaginary universe through a portal. The two embark on a lengthy and seemingly pointless journey to shrink the fan's plug down to normal size and plug it into an outlet in the brothel.

Volume 4[]

Team Sleuth learns that the nectar that DMK bleeds can be used by friendly bees to create Impetus Combs, which fuel special attacks called Comb Raves. Though they no longer possess weapons, the detectives figure out ways to elevate DMK's blood sugar and damage him, allowing the bees to create three Impetus Combs. The three ADs use them to do their Triple Truffle Shuffle Comb Rave, defeating DMK's first form.

Upon entering his second form, DMK removes blood sugar as a weakness by curing his diabetes with streams of dextrose. Three members of Team Sleuth (PS, PI, and ZAD) use their Gambit Schemas to turn into candy-themed monsters, giving them extra abilities. AD feels left out because he doesn't have a Gambit Schema, so he leaves the battle to go play the Game of Life with Death. FAD also departs, intending to go back to MK's office and kill MK.

At the brothel, HD and NB manage to resize the plug using portals that link between the brothel and trucks in the imaginary city, but they learn that the brothel's outlet is not powered. To turn on the electricity, they must defeat the brothel's owner, MK's female counterpart Madame Murel (MM). Death is called away from the Game of Life to aid PS in battle, leaving AD alone in the game's world as he gets married to a woman named Wifehearst, has a son named Sonhearst, and gets rich from running various criminal schemes. MK flees from FAD and enters the brothel's kitchen, where he is able to steal a Comb Rave intended for PI and give it to DMK instead. DMK's Fill 'Em with Daylight attack is so powerful that it tears the universe in half.

Volume 5[]

The universe is sewn back together by GPI using the fan's cord as thread and the Ham Needle from the imaginary city as the needle. HD and NB fight MM and kill her with a Double Comb Rave, allowing them to turn on the power; unfortunately, due to GPI's use of the fan cord, the electric current must traverse the length of the universe twice before it reaches the fan. MK acquires MM's Gravity Brassier, which lets him increase his mass. He kills FAD and continues to increase his mass, allowing him to easily shrug off attacks from HD, NB, and an increasing number of their allies, and strengthens his gravitational pull until he becomes the center of a supermassive black hole that threatens to consume the entire imaginary universe.

In the Game of Life, AD's life takes a tragic turn when Wifehearst is killed by thugs, his criminal empire is destroyed, and Bathearst (Sonhearst after becoming a vigilante) drowns during a covered wagon journey. Having lost everything, he kills himself, ending the game and returning him to the Chicago Overcoat. His sad story increases DMK's emotional level, which turns out to be his new weakness. During the battle with DMK, ZAD performs an ill-fated combat move that causes him to fall into a prison, where he dies. Meanwhile, Death has trouble trying to keep the increasing number of dead characters from leaving the afterlife through the exit door.

The time-traveling PI duplicate further splits himself into past and future selves, both of which sacrifice themselves to perform the Temporal Replicollision Comb Rave and defeat DMK's second form. DMK regenerates into his final form, now vulnerable only to the righteous fires of charisma. To defeat him, PS uses the eighth and final Impetus Comb to fuel the ultimate Comb Rave, Sepulchritude, transforming him into a diplomatic warrior with charisma powerful enough to fight DMK.

PS defeats DMK, but the monster deploys a Fetal Seedpod which will turn into another DMK if not destroyed. Sepulchritude wears off, leaving PS unable to attack the Seedpod before it and DMK are sucked into the ever-increasing black hole. Through an elaborate gambit involving the destruction of the moon, a bust of Snoop Dogg, and the fan (which is now running due to the black hole's temporal effects on the electric current), PI is able to deal a near-fatal blow to the Seedpod, and PS sacrifices the precious candy corn he found at the start of his adventure to finally kill DMK.

The moon lands on top of MK and pushes him out of the Gravity Brassier, destroying the black hole and sending everything within it flying. MK is impaled atop the Ham Needle's antenna and dies, dropping the Megaton Key. It is picked up by AD, who has merged with ZAD and FAD to become the strongest man in the world. PS is on the verge of death due to the effects of using Sepulchritude, but he is saved when HD kisses him on the cheek, restoring his will to live. The detectives return to their office building, where AD opens the door and allows Team Sleuth to finally leave.


With the afterlife's exit door now firmly sealed by a contrabass clarinet, MK is left forever unable to return to the living world. The four kingdoms celebrate a new era of peace in a ceremony observed by the Weasel King and his new wife, MM. PS, AD, and PI, still working as a team, patrol the Real City Streets in search of their next case. The story ends with them "Posing as a team," with a link to a gif that shows Death pushing his game cabinet toward Mobster Kingpin.

Print release[]

Main article: Books § Problem Sleuth

Problem Sleuth was released in print as a five-volume paperback book series published by TopatoCo, with the first volume released in April 2010 and the final volume released in October 2013. The volumes listed above are based on how the story was partitioned into these books.


  • Problem Sleuth is the first adventure to use color in its art as well as the first to use animated GIFs alongside still images. It also has the dubious honor of being the first adventure to be completed, as both of its predecessors (Jailbreak and Bard Quest) were initially abandoned before reaching an ending.
  • As one of the donation-funded non-canon commands, Andrew Hussie created a mapMspa icon of the Problem Sleuth world showing most of the key locations and the ways they connect.
  • Problem Sleuth was used as the theme for a puzzle in the 2010 MIT Mystery Hunt.
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