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
  • Chris Connor, IL, has won $3,493

    Chris Connor, IL, has won $3,493

    "First of all, I like the weekly themes, the quick return of tiebreakers, and prize checks. And, I also enjoy the sizeable checks and payoffs."
  • Ed Dansereau, MA, has won $16,633

    Ed Dansereau, MA, has won $16,633

    "I want you to know how much I enjoy your word success puzzles, win or not. It sure keeps my mind alert."
  • Deb Moore, MI, has won $73,076

    Deb Moore, MI, has won $73,076

    "You earn while you learn."
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