Questions need to be determined by trial and error. Successes will be noted but failures are not. Take the $100 question as an example:
Desired question: “What George Orwell novel talks about Big Brother?”
There are 18 possible success flags for the question:
- First word starts with W
- First word is “What”
- Second word starts with G
- Second word is “George”
- Third word starts with O
- Third word is “Orwell”
- Fourth word starts with N
- Fourth word is “novel”
- Fifth word starts with T
- Fifth word is “talks”
- Sixth word starts with A
- Sixth word is “about”
- Seventh word starts with B
- Seventh word is “Big”
- Eighth word starts with B
- Eighth word is “Brother”
- Word count is 8 words
- Overall character length (not including question mark) is 48 characters
In order, those flags (when correct) will return the words:
- Youth
- Heresy
- Yielding
- Cowardice
- Ennui
- Complaining
- Contrition
- Yawning
- Complications
- Heredity
- Oddity
- Powerlessness
- Entertainment
- Flavor
- Narration
- Ingenuity
- Grace
- Delightfulness
When the proper question is posed, an answer box will show up so that the solver can submit the title “NINETEEN EIGHTY FOUR”. Upon submitting that, the solver will be awarded a seemingly nonsensical prize of BILMSKCXWCNEP.
The remaining questions work in the same way. Questions, answers, and prizes are as follows:
| Dollar | Question | Answer | Prize |
| $100 | What George Orwell novel talks about Big Brother? | NINETEEN EIGHTY FOUR | BILMSKCXWCNEP |
| $200 | What Oscar Wilde novel involves a portrait by Basil Hallward? | THE PICTURE OF DORIAN GRAY | PIBNQDJCCYEFE |
| $300 | What Harper Lee novel features lawyer Atticus Finch? | TO KILL A MOCKINGBIRD | KRCHCMEDYEBCC |
| $400 | What novel was initially titled The Innocent Voyage? | A HIGH WIND IN JAMAICA | EKDYIFCLEPCHC |
| $500 | What Kurt Vonnegut novel takes place in Dresden? | SLAUGHTERHOUSE FIVE | XYCKJLZCCIYOY |
The next thing to notice is that the flag success words start with unusual letters. In fact, the initial letter for each success word maps as a cipher text to the answer itself. (In the first example, initials from the success words YHYCECCYCHOPEFNIGD maps to NINETEENEIGHTYFOUR.) This mapping is consistent through all five answers and can be used to help narrow down novel titles for questions that haven’t been answered.
Further, once the prize is translated this way, the five prizes can be read via a simple route cipher to read WHATBOOKANSWEREDFINALJEOPARDYSEPTEMBERSEVENTEENTHOFTWENTYEIGHTEEN? The answer is EAST OF EDEN.