1. Ready to start winning?
    Fill out the form to purchase our 3 Month Newsletter Subscription and a chance to play and win thousands of dollars every week!

  2. Please type your full name.
    Invalid email address.
  3. Invalid Input
    Invalid Input
  4. Invalid Input
    Invalid Input
  5. Invalid Input
    Invalid Input
  6. Choose a Subscription Length



    Invalid Input
  7. Invalid Input
  • Print Your Puzzle

    Print your entry puzzle at home.
  • Complete It!

    Enjoy & complete your puzzle at home. Fill in the entry form and include your entry fee.
  • Mail Your Puzzle

    Send your puzzle back to us. Include your entry fee & completed entry form.
  • Win Cash Prizes!

    Accurately complete the puzzle to win cash prizes.
  • 1
  • 6 Month
    Challenging Times Subscription
    $25

    Buy Now
  • 12 Month
    Challenging Times Subscription
    $40

    Buy Now
  • 1
  • Carole Shaffer, MI, has won $28,830

    Carole Shaffer, MI, has won $28,830

    "I’m so glad you somehow found my name."
  • 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!"
  • Earle Smith, MA, has won $3,059

    Earle Smith, MA, has won $3,059

    "Challenging Times has been a rewarding, stimulating and therapeutic experience."
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11