Halloween: The Game Chapter 5: all 6 challenges
Known in-game as Into the Shadows. 19.1% of Steam players have finished it.

If a chapter restarts instead of saving. Patch 1.0.4 fixed the crash after finishing a story chapter. If a chapter still ends on a black screen and loads again from the start, its challenges and XP were not saved and the next chapter stays locked. What to do if it happens.
Tick these off as you go on the challenge tracker, which keeps the record in your browser even when the game does not.
Chapter 5 swaps residents for police officers, which changes the pace: they carry flashlights and they look for you. Several of its challenges are about handling that rather than about executions.
One challenge here is genuinely unreliable. The Loomis stealth challenge can fail on runs where he never detects you, so its real condition is stricter than its description. If you fail it without being seen, you are probably not doing anything wrong.
Watch all 6 Chapter 5 challenges done
Into the Shadows, every challenge
Halloween: The Game Chapter 5 ALL CHALLENGES Guide Walkthrough! Into The Shadows
JROID
One run through the whole chapter, every challenge in order. It is the quickest way to see where each target and object actually is before you start.
Challenge 1Two flashlights at once
Goal: Disable two officers' flashlights with a single use of the ability.
You need two officers standing together. A reliable pair appears on the north side, just before the sewer entrance on the right. Use the ability once while both are in range. Disabling both lights is enough; they do not need to be fully drained.
Challenge 2Pitchfork execution
Goal: Execute a police officer with the pitchfork.
Leave the spawn area, turn right, and continue a short way. The pitchfork leans against a house wall just left of a parked car.
Improvised weapons
Challenge 3Three residents
Goal: Take down three residents before escaping.
Head right from the restroom and check the houses along that side. Three is easily reached without crossing the map.
Challenge 4Officer in Wallace's house
Goal: Deal with a police officer inside the Wallace House at Tier 3.
Build to Tier 3 first. If no officer is inside when you arrive, make yourself briefly conspicuous near the officers outside to draw one in.
Stalk tiers
Challenge 5Escape undetected by Loomis
Goal: Get out without Loomis detecting you.
This one is flaky and can fail on runs where Loomis was never alerted. Two things matter. First, leave through the sewer: escaping by Shape Jump tends to fail it, so do not jump out. Second, bodies: Loomis finding one can fail the challenge even though he never saw you. Leave nothing where he walks.
Challenge 6Disable the police car
Goal: Put the police car out of action.
Hit it with your melee weapon a few times. It cuts out with a small explosion and starts smoking, and that is the completion. The pop-up often does not appear at that moment. It lands when you escape, so do not keep hitting a car that is already dead.
Full walkthrough for this challenge (why nothing pops when the car dies, and where the cars are)
Environmental destruction
Story mode difficulty runs Normal, Hard, Boogeyman. No challenge asks for a particular setting. What each setting changes.
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