How It Works

  • Each week we will send you the Challenging Times by first class mail.
  • This publication contains 5 new puzzles EVERY WEEK, predominantly composed of Word Search and Word Success puzzles. For our newest entry puzzle click here
  • You can solve the puzzles just for fun or you can pay the entry fee(s) and enter them into the cash prize contest - pitting your skills against the other puzzlers in our membership. 
  • Not only will you have access to more puzzles by subscribing to Challenging Times, but you will have the opportunity to win cash prizes too - UP TO $3200 PER WEEK! 
  • The cost is very reasonable too - less than 80 cents per week for a year's subscription! So why don't you subscribe today ? 



  1. Winning depends on a contestant’s skill. This is not a sweepstakes or a drawing. 
  2. The entry fee is stipulated on each entry form. Each tiebreaker costs $1 for handling and judging. All puzzles have due dates. 
  3. Approximately 75-85% will qualify for the first tiebreaker. 20-30% will qualify for the second if required. 2-10% will be winners. 
  4. All prize checks will arrive in contestant’s mailbox approximately 8 weeks after the original due date. If the puzzle goes to a second tiebreaker, it will take about 13 weeks from the original due date. 
  5. Winners may expect prize checks up to the maximum stipulated amount for each puzzle with an average of $25-$75, depending upon the skill of the contestants relative to the difficulty of the puzzle. 
  6. Judges are employees of CM Publications, Inc. and a minimum of two people judge the entries. Entries are scored manually by using a key. 


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  • 1
  • Suzanne Borash, MN, has won $46,945

    Suzanne Borash, MN, has won $46,945

    "I have always loved doing word puzzles and learning about different topics. Challenging Times offers the opportunity to do both. I particularly enjoy Winning Words because it’s fun researching the answers and unscrambling the letters. The Presidents Payoff, States, and State Capitals puzzles help sharpen memory…. Thank you, Challenging Times, for making life more fun!"
  • Midge Rappenecker, IA, has won $2,582

    Midge Rappenecker, IA, has won $2,582

    "Keep up your good work & hurrah for winning 3 weeks in a row."
  • Mary Salvatore, IL, has won $60,818

    Mary Salvatore, IL, has won $60,818

    "Contests are judged fairly and prize checks arrive promptly. It’s exciting to open the mail and find a prize check."
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