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Sanding a pickguard?

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Yes, you always want to have a roughed-up surface to paint on. I would suggest sanding with 400-600 grit and then scuffing it with a Scotchbrite pad. I haven't had the greatest luck with painting a pickguard, but you might try the Fusion paint by Krylon, it's made for plastic. I would suggest Krylon Industral, but that can be hard for the general public to get. It works great on plastic automotive trim though.

Good luck.

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