Conundrum may refer to:

In literature:

• Conundrum (Doctor Who), an original novel written by Steve Lyons
• Conundrum (novel), a Dragonlance fantasy novel by Jeff Crook
• Conundrum, a memoir written by Jan Morris
• Conundrum Press, two book publishing companies in North America

In other fields:

• "Conundrum" (song), an instrumental song by Jethro Tull
• "Conundrum" (TNG episode), a fifth season episode of Star Trek: The Next Generation
• The "Conundrum", a mountain unicycle made by Surly Bikes

In general:

• Conundrum, a puzzle or a riddle designed to test for lateral thinking