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Many fails are results of sheer idiocy. Luckily, it makes them funnier. While several of them are brought upon by Henry himself, others can contribute to the idiocy as well.

Unmarked spoilers ahead!


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    Breaking the Bank 
  • In the legacy version, one of the six choices is to use explosives to get into the bank. However, when Henry prepares to blow them up, it doesn't work.
    You'd Expect: Henry to play the waiting game and wait for the bombs to blow up (which they do).
    Instead: He decides to check on the bombs to see why they didn't explode.
    The Result: They blow Henry up, resulting in a FAIL.
  • Ted McAdams and Winston Davis find a money bag that Henry is secretly using as a disguise. They decide to throw it into their truck.
    You'd Expect: One of them to notice something up upon presumably feeling something within it that's shaped like a person (instead of a bunch of money).
    Instead: They don't find out until Henry leaves the bag and is caught by the vault's security system. Though it doesn’t really matter because he still gets caught and arrested anyway.

    Escaping the Prison 
  • The beginning of the game's story is built on this. A new prison guard, Dave Panpa, has just found a package that should be delivered to Henry.
    You'd Expect: Dave to check the package, like a normal guard or policeman would do.
    Instead: He doesn't do that at all and just delivers it straight to Henry.
    The Result: The cake within the package has an item that would help Henry escape, thus setting the rest of the series in motion. Additionally, it is shown in Stealing the Diamond that Dave's failure to check the package or stop Henry from escaping ended up costing Dave his badge, forcing him to find work as a security guard at the Museum.
  • After finding himself on the roof of the prison in the Sneaky Escapist route, Henry finds a box containing things that would help him get down. One of them is a backpack which seemingly contains a parachute.
    You'd Expect: Henry to check the contents of the bag to see if it really contains a parachute.
    Instead: The closest thing to a check is a weight check on the back, before Henry just jumps off.
    The Result: As it turns out, it's just a regular backpack, and Henry is sent plummeting to the ground with its contents (including a bowling ball which finishes him off). This triggers a FAIL.
    FAIL screen: I think that was just a regular backpack. See what happens when you assume?

    Infiltrating the Airship 
  • Many FAILs from the Government Supported Private Investigator route can turn a playthrough into an avalanche of stupidity.
    • Upon entering through the hatch of the Toppat Clan's airship, Henry can use the Transdimensionalizer to sneak past several Toppats during their meeting.
      You'd Expect: Henry to flip the switch up to the 3rd dimension, so he can move out of the 2D plane the game is made in and evade the Toppats' sight.
      Instead: He flips the switch down to the 1st dimension.
      The Result: The 1st dimension's limits on Henry's mobility bar him from the 2nd dimension, causing a FAIL.
      FAIL screen: You went to the 1st dimension. That's okay, just flip the switch to get back to... oh, right.
    • If Charles chooses to use a gravity manipulator on Henry to help him float across a gap, he unwittingly increases gravity's effect on Henry (or did he make Henry go down more?), and then asks Henry if it worked, hearing no response.
      You'd Expect: Charles to press the button he didn't previously press in order to stop Henry from getting crushed by his own weight.
      Instead: He presumably fails to deduce what happened to Henry.
      The Result: The FAIL screen pops up shortly after Henry's predicament is cut to.
    • After helping Henry cross the gap, Charles can choose to shoot down Wilhelm Krieghaus so Henry can steal his key card.
      You'd Expect: Charles to single out the Toppat and gatling-fire directly at him.
      Instead: He sweeps the firing gun near the entire room's floor.
      The Result: Henry dies with Wilhelm, resulting in a FAIL.
    • Later, after Henry gets evidence and enters a vent, it turns out there's an electric trap preventing him from getting to the other side. He can tell Charles, who has just hacked into the Airship's power grid, to shut off the power.
      You'd Expect: Charles to specifically shut off the electric trap.
      Instead: He turns off the entirety of the airship's power, even though he removes nothing but the trap's power should Henry tell him to reroute the power.
      The Result: The airship falls out of the sky and presumably crashes, triggering a FAIL.

    Fleeing the Complex 
  • At the very start of the game, Henry can choose to play dead in an attempt to escape The Wall. Grigori, the right-hand man of Dmitri, notices him falling over.
    You'd Expect: Grigori to check Henry's pulse to see if he's really dead.
    Instead: He falls for it. Granted, the option still leads to a FAIL, as Dmitri immediately tells Grigori through radio to toss Henry's "corpse" through the trash chute, killing him for real, but still.
  • In the Ghost Inmate route, Henry finds himself near an elevator shaft which he has to get down in order to proceed. One way he can is a bungee jump.
    You'd Expect: Given that Henry is known to have hammerspace, he could use a specialized bungee rope to get down, like the wire in Unseen Burglar in Diamond.
    Instead: He uses a normal rope.
    The Result: He ends up ripping his body in half, causing a FAIL.
    FAIL screen: Did... Did you just bungee jump with a plain rope?
  • Later on, after having made it to the docks and made it past Nicholai Dytrim and Matteus Guardsmith, Henry has the possibility of using the S.S. Annie to finally escape The Wall.
    You'd Expect: Henry to try subduing the entire crew before hijacking the ship.
    Instead: He goes straight for the captain, not considering about the idea that a cargo ship would have lots of people staffing it.
    The Result: After having made the ship leave the docks and seemingly succeeded, Henry is suddenly attacked from behind by Milosh Krakowski, causing it to FAIL.
    FAIL screen: Did you think none of the crew would notice an unscheduled departure?
  • In the International Rescue Operative branch, one choice at the helipad is for Henry to fall backwards off the edge.
    You'd Expect: Henry to have told Charles to stay away from the helipad, so Henry can leap off the fire exit staircase and Charles can maneuver his helicopter to rescue Henry in midair (something Charles proves to be capable of in the Triple Threat ending of Completing the Mission).
    Instead: Henry suddenly jumps off without coordinating anything about it with Charles.
    The Result: Charles realizes Henry's plan too late. Henry falls to his death and Alex Kempter blows up Charles with a rocket launcher, resulting in a FAIL.
  • In the The Betrayed branch, Wallace Pemberton is an undercover agent for the Toppat Clan who can be chosen as the clan's first method of helping Henry escape the Wall.
    You'd Expect: Him to haul Henry away under the guise of being the guard who catches the latter trying to escape.
    Instead: He LOUDLY exclaims "Hey, Henry! It's me! I'm undercover! I'm here to break you out!".
    The Result: The actual guards in the cafeteria hear everything he says, likely leading to him and Henry getting captured and causing a FAIL.

    Completing the Mission 
  • In the Free Man route, the now-cyborg Right Hand Man desires revenge against Henry Stickmin for arresting his former boss.
    You'd Expect: Him to just kill Henry immediately upon capturing him. Given that this is the same guy who singlehandedly infiltrated an airship full of dangerous criminals and brought him to near death to the point that he's forcefully rebuilt as a cyborg, Henry is certainly a huge threat to the clan if he stays alive.
    Instead: He just imprisons him within their spaceship before leaving him be without any surveillance whatsoever.
    The Result: Henry successfully escapes the ship and disables its reactor core in the process, resulting in RHM along with the remaining Toppat members stuck in space with no way of going back to earth.
  • Near the Master Bounty Hunter ending, amidst the Toppat Clan's panic over the Right Hand Man's capture, Sven Svennson is the only Toppat who can launch the rocket into orbit.
    You'd Expect: Sven to sit his ass into the cockpit's chair and activate the emergency launch protocol, akin to when Henry hijacks the rocket in the Stickmin Space Resort route. Even though the majority of the clan isn't onboard and might get arrested by the Government, the orbiting station would be able to operate with whoever's already on board and beam up any escaped members.
    Instead: He calls another Toppat and urges that they all need to leave immediately.
    The Result: Whoever Sven called rebukes him, and he is arrested along with most of the other Toppats.
  • Near the Valiant Hero ending, Henry is pulled out of his and Charles' escape pod by a desperate Jacked Hughman. Charles leaves the escape pod momentarily to shove Jacked away and rescue Henry.
    You'd Expect: Him to leap back into the escape pod with Henry in his arms.
    Instead: He throws Henry inside, allowing Jacked to tackle him away from the pod.
    The Result: The escape pod seals and launches itself with only Henry inside it, and Charles tragically dies when the Toppat orbital station's core explodes.
  • Much like the Government Supported Private Investigator route in Infiltrating the Airship, the choices made in the Toppat Civil Warfare route (both the decisions in the story AND the fails) are seriously stupid.
    • After Ellie Rose reveals to the entire Toppat Clan that Henry abandoned her in the Wall, everyone decides to get Henry to Walk the Plank off the airship to his death. However, Henry fights back and tosses Reginald Copperbottom overboard.
      You'd Expect: For someone to try and kill Henry in retaliation before sending the Right Hand Man Reborn to rescue Reginald.
      Instead: Nobody does anything until after the Right Hand Man flies down to grab Reginald and get him to safety.
      The Result: Because they didn't leave rescuing Reginald for later and killed Henry when they had the chance, Henry and his loyalists use an escape pod to get out of the airship after the final choice set. Said escape pod crashes into the Right Hand Man's face just after he had grabbed Reginald, killing both of them anyway and forcing Ellie to take Reginald's spot as leader of the Toppats.
    • After THAT moment, Ellie grabs an AK-47 and threatens to shoot Henry if he doesn't jump off the airship. One of the options for Henry to get out of this mess is a chainsaw.
      You'd Expect: Henry to use it to kill as many Toppats (and potentially Ellie) as he possibly can. Even if he dies and still result in a FAIL, these Toppats would go down along with him.
      Instead: He uses the chainsaw to cut the plank he's on off the airship in an attempt to invoke Gravity Is a Harsh Mistress.
      The Result: Because his world doesn't run on Looney Tunes physics, he falls to his doom, still causing a FAIL.
    • In the "Good Gents" option, Henry and his loyalists invade the bridge of the Airship to take back the leadership of the clan by defeating Ellie, Reginald, and RHM.
      You'd Expect: Considering how Henry betrayed Ellie back at the Wall, making her vengeful, and even though he did fake his death by using a helicopter-propelled hat, she can simply recognize Henry with his golden dollar top hat and potentially use the Force at Henry, to kill him by suffocation, while RHM would take care of the others.
      Instead: She basically does nothing after the Right Hand Man angrily shouts and fires the laser at the gang, cutting off Henry and Geoffrey.
      But Then Again: Considering that this results in a FAIL, it's very likely she already did this or shot Henry quickly afterwards but it wasn't shown when the FAIL interrupts them.
    • One plan of Geoffrey Plumb's in the last choice set is called "Midnight Surprise", where Henry and his loyalists plant bombs within the airship to blow it up at 12 AM.
      You'd Expect: The four to retreat in an escape pod (like they do for the correct choice, "Deuces!") a few seconds before midnight.
      Instead: They trigger the explosions while they're still boarding the airship.
      The Result: Henry's squad is blown up with the rest of the airship division, resulting in a FAIL.
      FAIL screen: Ah, just like old times.
      That was a poorly thought out plan...

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