Usually means: Cunningly deceitful or crafty behavior.
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We found 21 dictionaries that define the word guileful:

General (19 matching dictionaries)
  1. guileful: Merriam-Webster.com
  2. guileful: Oxford Learner's Dictionaries
  3. guileful: American Heritage Dictionary of the English Language
  4. guileful: Collins English Dictionary
  5. guileful: Vocabulary.com
  6. Guileful, guileful: Wordnik
  7. guileful: Wiktionary
  8. guileful: Webster's New World College Dictionary, 4th Ed.
  9. guileful: The Wordsmyth English Dictionary-Thesaurus
  10. guileful: Infoplease Dictionary
  11. Guileful, guileful: Dictionary.com
  12. Guileful: Online Plain Text English Dictionary
  13. guileful: Webster's Revised Unabridged, 1913 Edition
  14. guileful: Rhymezone
  15. Guileful: AllWords.com Multi-Lingual Dictionary
  16. guileful: Webster's 1828 Dictionary
  17. guileful: Free Dictionary
  18. guileful: Mnemonic Dictionary
  19. guileful: Dictionary/thesaurus

Business (1 matching dictionary)
  1. guileful: Legal dictionary

Computing (1 matching dictionary)
  1. guileful: Encyclopedia

(Note: See guile as well.)

Definitions from Wiktionary (guileful)

adjective:  Full of guile; treacherously deceptive.

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