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I mean, I've not tried it before but it seems like a good idea to make bigger plugged holes more likely to remain sealed so I guess I might try it next time I'm not in a hurry or struggle to get a plug to work. I'm not going to crack open my glue just for shits and gigs but once the plug is in, dabbing with superglue or vulc glue might help keep it there.
hippy
I was also interested in this. Did you get anywhere with it? Feels like it would be pretty awkward getting a plug in whilst it's covered in vulcanising solution etc but it's also awkward having a plug fly out at high velocity whilst trying to pump the tyre up again.