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There's something really counter-intuitive about making a hole larger in order to fix it. Indeed, I spent a good 5 mins shoving the pointed tool through the once-small hole. Got the worm in accidentally pulled it out when trying to cut off the excess on the outside. Will have another attempt later once I get all the jizz cleaned up.
You can push a tyre worm in. You are meant to make the hole bigger with these. Just shove it in. Timidness is a real problem.