Within the Otherworld version of the Shepherd House are four puzzles which must be completed in order to exit. The puzzles are symbolic of the inner torment that each member of the Shepherd family suffers and offer a glimpse into their background.
This puzzle is found on the first floor and is characterized by a set of masks that must be placed correctly upon two corpses.
Above one corpse is the phrase "To hide her pain this mask she did wear..." and above the corpse on the other side is "Behind this mask her heart was laid bare." Scattered throughout the house are three masks:
Through Alex Shepherd's observations of his mother, the Indifferent Mask can be identified to be the mask that "hides her pain", and the Frowning Mask to be how her "heart was laid bare". This puzzle represents the inner sadness that Lillian Shepherd feels, and her attempts at hiding it from her family.
In what used to be Alex and Josh's room is a puzzle involving a large clock and four windows. On the wall is written the following poem:
- Nobody saw when you were crying on your bed.
- I wanted to help you, but I hid myself instead.
- The ticking of a clock, then suddenly not.
- Fate left me here. In shadow I will rot.
- Under my covers, the darkness kept me in.
- Only the daylight can save me from my sin.
In the 2F bathroom, Alex finds a Robbie the Rabbit toy in the bathtub. After reading the poem and setting the correct time for the clock on the opposite wall, four windows will be exposed. The proper time can be discerned by reading a memo from Alchemilla Hospital within the same room. One of the windows is brightly lit, and in the poem, this can be inferred as "daylight." In order to solve the puzzle, Alex must place the Robbie stuffed toy on the window with the light. This puzzle represents Joshua Shepherd's inner thoughts about his partial treatment and his guilt towards Alex.
Within the Attic of the Hell House, Alex will find a jacket, similar to the one he wears, with three spaces reserved for placing medals. The three medals are found in the Attic and the room before it:
- Heart of Darkness Medal: For permitting others to suffer
- Vile Acts Medal: For atrocities committed
- Fallen Star Medal: For dereliction of duty
The correct order can be determined from the Certificate of Release or Discharge from Active Duty found on one of the tables in the secret room in the Attic of the Shepherd House before transition to the Otherworld. The certificate mentions the following: Good Conduct Award, Purple Heart, Silver Star. Therefore, the correct sequence of the Hell House versions of the awards is Vile Acts Medal, Heart of Darkness Medal, Fallen Star Medal; placed right-to-left from the point of view of the player, or left-to-right from the point of view of the awardee.
If you examine the box that the Fallen Star Medal is found in, there are recesses that the other two medals fit into. Through this, one can also discern the order in which they must be placed.
This puzzle most likely represents Adam Shepherd since the Certificate of Release on which this puzzle is based is his as well as the medals awarded.
In the Otherworld Shepherd House, Adam's hunting room in the basement remains relatively unchanged, with only minor changes. The most notable change is the hanging, decapitated Schism hanging the corner of the room. It's head on the table serves as the puzzle.
Scattered about the Hell House are three knives:
To solve the puzzle, the knives must be placed in their respective places, and with the outline of the previous knives easily seen, it is readily apparent where the knives are to be placed. The Butcher Knife should be placed on the board on the upper left. The Cleaver Knife should be placed on the board on the mid right. And the Bogeyman Knife should be placed on the Schism's head.
This puzzle likely represents Alex Shepherd. The beheaded Schism can be attributed to Alex's lobotomy and the sacrifice the Shepherd family was destined to undergo. The blades also all resemble those that past Silent Hill characters have used to murder, so it may hint Alex's hate towards his father or his killing of Josh. Some speculate that it may also relate to Adam Shepherd, as it involves his affinity to hunting and his use of the knives.
- The cross the corpses of the "Mask Puzzle" are attached to is similar to the device that holds Lillian Shepherd in the Penitentiary.
- Although three masks are found in the house, only two are needed for the "Mask Puzzle".
- The memo from the hospital found in the Hell house version of Josh's room is the same one found in the Operation Theatre, the very first room in Alex's nightmare.
- The Vile Acts Medal employs the shape of Pyramid Head's helmet.