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If you paint over flaking paint, the new paint will stick to the old flaking paint rather than to the chair and the old and new paint will come off together, and you'll be back where you started, with a chair with flaking paint. You need to remove the flaking paint, a stiff brush sounds fine, scrub hard.Spray paint is excellent for wicker, you might see if you can get a spray primer too, it could stick better than regular paint
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