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
  • Pat Walsh, IN, has won $28,797

    Pat Walsh, IN, has won $28,797

    "As a long-time contestant in through-the-mail puzzles offered by various organizations, I have been happiest with Challenging Times as a sponsor. Your various puzzle formats, with their mixed degrees of difficulty, are interesting and challenging. Best of all, I know that I can count on you to send your puzzles and tiebreakers on schedule… And I really appreciate the way you pay your prizes promptly."
  • Dan has won $25,340 so far!

    Dan has won $25,340 so far!

    Challenging Times has been an exceptional puzzle club that I have been amazed with over the last 13 years. If anyone is willing to challenge their mind with puzzles and earn supplemental income then Challenging Times is the way to go!
  • 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."
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