Usually means: Driving a truck without its trailer.
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We found 3 dictionaries that define the word bobtailing:

General (3 matching dictionaries)
  1. bobtailing: Collins English Dictionary
  2. bobtailing: Wordnik
  3. bobtailing: Wiktionary

(Note: See bobtail as well.)

Definitions from Wiktionary (bobtail)

noun:  A short, or deliberately shortened tail.
noun:  An animal that has a bobtail, such as certain canines or nags.
noun:  (agriculture) A tractor which performs without its trailer.
noun:  A tractor-trailer that is relatively short in length.
noun:  The tractor unit of a semi-truck without a trailer
noun:  (poker, often attributive) An open-ended straight or four flush.
noun:  A bobtail squid
noun:  A bobtail skink
verb:  (agriculture) To drive a tractor without its trailer.
verb:  To drive a truck or other vehicle without its trailer.
▸ Also see bobtail


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