B757 FLC HAS DEICE TRUCK BOOM HIT WING FLAP TRACK FAIRING.

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PUSHED BACK ABOUT 15 FT FROM GATE TO DEICE UPPER WING SURFACE. ACFT WAS STOPPED; CONNECTED TO TUG; WITH PARKING BRAKE SET (ELECTRIC HYDS ON; ENGS HOT STARTED). L WING DEICED WITH NO TROUBLE. DRIVER ATTEMPTED TO GO UNDER R WING. BOOM/BASKET STRUCK THE OUTBOARD FLAP TRACK FAIRING (SO CALLED 'CANOE'). DAMAGE WAS CONFINED TO THE CANOE. BEFORE HE BEGAN DEICING; THE DRIVER/OPERATOR SAID HE PLANNED TO 'TAKE CARE OF' A THIN FROST LAYER ON THE BOTTOM SURFACE OF THE WING. I TOLD HIM THAT FROST ON THE BOTTOM OF THE WING WAS OK; THAT ONLY THE TOP SURFACE NEEDED DEICING. I DON'T KNOW IF HE HAD BEEN TOLD TO SQUIRT BOTH TOP AND BOTTOM SURFACES. HE MAY HAVE BEEN TRYING TO POS THE TRUCK TO DO THE BOTTOM. OR HE MAY HAVE BEEN IN A HURRY. OR MAYBE THERE WERE OTHER (CURRENTLY UNKNOWN) FACTORS WHICH LED TO HIS DECISION TO DRIVE UNDER THE WING INSTEAD OF AROUND IT. IF HE WAS WORKING ALONE AND NOT WITH A PARTNER/SPOTTER; THIS TOO COULD BE A FACTOR. ALTHOUGH OTHER FACTORS MAY BE IN PLAY; THIS APPEARS TO BE RELATED TO GAPS OR SHORTFALLS IN TRAINING; SUPERVISION; OR EXECUTION OF PROCS. AT THIS POINT; IT'S TOO EARLY TO TELL.