Usually means: Unaware and unprepared; taken by surprise.
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We found 6 dictionaries that define the word caught napping:

General (2 matching dictionaries)
  1. Caught Napping: Dictionary of Phrase and Fable (1898)
  2. caught napping: TheFreeDictionary.com

Computing (1 matching dictionary)
  1. caught napping: Encyclopedia

Medicine (1 matching dictionary)
  1. caught napping: Medical dictionary

Miscellaneous (2 matching dictionaries)
  1. caught napping, Caught Napping: Idioms

Definitions from Wikipedia (Caught Napping)

noun:  a 1959 comedy play by the British writer Geoffrey Lumsden.

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