UA 777 too heavy for two tugs
During flight tests of the 747-8F, they were operating one aircraft out of Victorville. They put the 747 in a hanger to do some work, when it came time to move it back out the first tug wasn't powerful enough to move it, so they parked that tug outside the hanger at got a bigger one. Except that they didn't move the first tug far enough - as they pulled the 747 out of the hanger, one of the engine nacelles struck the first tug...

Join Date: Nov 2004
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Used to have trouble pushing back 747's at Kai Tak. The problem was the slopes built into the ramp area presumably for drainage in tropical downpours and built long before pushbacks were required. A 747 rolled back about 15-20 feet to the low point before the main gear ran onto the upward slope to the crown of the taxiway which required some serious grunt from the tug and a driver who kept the tow bar dead straight until the main gear neared the crest of the taxiway. On a wet ramp slick with oily droppings it was a real problem and there were many incidents. It wasn't a tug power problem it was a lack of traction. I had a NWA 747 jackknife the tug and tow bar one morning after starting all 4 engines at the gate. No damage to the aircraft but a damaged tow bar a big hassle getting the tow bar unhitched from the tug at 90 degrees to the tow bar.. Eventually the airport authority cleaned the areas the tugs drove on and laid down an antiskid finish. Also I think it was required that engines be started on push back not beforehand.