• A riddle
  Riddle
  A riddle is a statement or question or phrase having a double or veiled meaning, put forth as a puzzle to be solved. Riddles are of two types: enigmas, which are problems generally expressed in metaphorical or allegorical language that require ingenuity and careful thinking for their solution, and...
  
   whose answer is or involves a pun or unexpected twist
• A logic
  Logic
  In philosophy, Logic is the formal systematic study of the principles of valid inference and correct reasoning. Logic is used in most intellectual activities, but is studied primarily in the disciplines of philosophy, mathematics, semantics, and computer science...
  
  al postulation that evades resolution, an intricate and difficult problem

Literature

• Conundrum (Doctor Who)
  Conundrum (Doctor Who)
  Conundrum is an original novel written by Steve Lyons and based on the long-running British science fiction television series Doctor Who. It features the Seventh Doctor, Ace and Bernice. A prelude to the novel, also penned by Lyons, appeared in Doctor Who Magazine #208...
  
  , a 1994 original novel written by Steve Lyons
• Conundrum (novel), a 2001 Dragonlance fantasy novel by Jeff Crook
• Conundrum, a memoir written by Jan Morris
  Jan Morris
  Jan Morris CBE is a Welsh nationalist, historian, author and travel writer. She is known particularly for the Pax Britannica trilogy, a history of the British Empire, and for portraits of cities, notably Oxford, Venice, Trieste, Hong Kong, and New York City.With an English mother and Welsh father,...
  
  
• Conundrum Press (disambiguation), two book publishing companies in North America

Other fields

• "Conundrum" (song), an instrumental song by Jethro Tull
• "Conundrum" (Star Trek: the Next Generation), a fifth season episode of Star Trek: The Next Generation
• The "Conundrum", a mountain unicycle made by Surly Bikes
  Surly Bikes
  Surly Bikes is a designer and importer of bicycles, frames, parts, and accessories based in Bloomington, Minnesota, established circa 1998. Surly is owned by and shares facilities with Quality Bicycle Products ....
  
  
• "Conundrum" NSA code word for Chrononaut Frank B. Parker in the television series Seven Days