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It means driving your truck without a trailer connectd to it Bob tailing is in reference to a tractor/trailer combination vehicle or the more common terms of big rig or 18 wheeler.' In the commercial truck driving sense the word tractor is another name for truck. When the trailer is uncoupled (unhooked) from the tractor and the tractor is heading for another destination without the trailer it is called, bob tailing.

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16y ago

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