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I need to run coaxial cable to another room and the original hole near the bottom of the wall got covered by a taller baseboard. Is it ok to drill through the baseboard?

There's still a hole on the other side of the wall because that side has a shorter baseboard. Is it best to drill from this shorter-baseboard side that still has a hole? I don't want to push the taller baseboard off its wall though.

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Perfectly fine to drill through a baseboard.

I would drill a pilot hole from the side that still has the shorter-baseboard. That gets you lined up without worrying about splitting the new baseboard or pushing it away from the wall. Then drill the full-size hole from the taller-baseboard side, centered on the pilot hole.

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