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Soften your earmolds. Soak them in hot water for a while (I know that seems counter-productive as it would "swell up" and make the hole even smaller, but it makes them (at least mine) more flexible. I do all my own tubing and I don't use any tools. You might have too much friction, so I wonder if using an oil (like baby oil) would help? I know the frustration - every once in a while I do have an earmold that just won't cooperate. It takes me more than a few tries when it's like that. Softening them seems to be what works for me.