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I saw it happen on a tour one time. The owner unbolted #8 to remove the distributor for repair and in about 20 minutes the pan was full of water. That convinced me to never break the torque on the head unless I am removing the head. Especially out on the road. Since then I don't use a clamp to hold the pop-out cable in place. I installed a standard length stud in the #8 position. Another option is to install a 1\4" spacer under the nut.
I remove the distributor every time I change oil and clamp it in a vice, clean it up, dress up the points and re-set the gap. This also prevents it from ever rusting in place.
Clamping the cable down was part of Henry's anti-theft design.
Tom Endy