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."
  • Sharon Sovereign, OR, has won $25,598 so far!

    Sharon Sovereign, OR, has won $25,598 so far!

    I have been playing Challenging Times contests for several years now. I had to end my full-time career as an accountant when my mother became too ill to live alone, and moved in with me. After she died in 2013, my husband of 54 years became ill, and I am now his full-time caregiver. Your puzzles keep my brain sharp, my spirits up, and provide a much needed respite from caregiving. And it's really fun to look forward to the mail each week for my new puzzles, and the money I win. I particularly enjoy the number puzzles. Thank you.
  • Katie Kappel, MI, has won $22,995

    Katie Kappel, MI, has won $22,995

    "Challenging Times has afforded me the opportunity and satisfaction not only of earning much needed money but also sharpen my memory and reasoning skill while spending many pleasurable hours completing the puzzles. I don’t know how I made it through our cold winters before discovering Challenging Times – what a great way to alleviate cabin fever while cashing in!"
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