Sounds stupid but......

I had same thing happen to me on two plugs over and over again. Most rear plugs on both sides. What made it worse was my engine would stall when the wire comes off (don`t know why, but if I pull ANY single wire off the plug it stalls). I have found that it is way too hot for those wires (I got no heat shields on manifolds) and the air between the plug and rubber boot expands and pushes the boot off. After installing flexible fiberglass heat sleeves over the wires - problem is gone.

Now that is something I never thought of because God knows its frickin hot back there.
 
Same thing happened to me on the #3 wire on the 440 in the Monaco. It seemed to snap into place fine but after a 5 minute drive it dropped off again. I didn't mess around and just got another set of wires and no issues since.
 
Same thing happened to me on the #3 wire on the 440 in the Monaco. It seemed to snap into place fine but after a 5 minute drive it dropped off again. I didn't mess around and just got another set of wires and no issues since.

Third set of wires (same brand though) and it is only #8 giving me fits...
 
try putting a small amount of epoxy on the end of the boot before you slip it on. the boot should still come off easily enough later to change the plug with a little twist.
 
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