Scrape the cedar wood to remove as much of the paint as possible with a paint scraper, exposing the bare wood underneath. This gives your primer and paint a surface on which to adhere.
Inspect any areas where you have caulked. If the caulk is old, loose or cracked, remove it and replace it with new.
Wash the cedar siding with a ratio of three parts warm water to one part liquid bleach in a five-gallon bucket. Add a teaspoon of dishwashing liquid.
Dip a stiff-bristled brush into the water and bleach mixture and scrub the entire area of the cedar siding, in order for the sealer and paint to stick. Do not use a power washer, because cedar is soft wood and the pressure of the power washer can easily damage the wood.
Rinse the cedar siding off with a water hose to remove the dirt that you loosened with the brush.
Allow the cedar siding to dry at least two weeks before you apply the sealant. The wood has to be completely dry or the sealant won't adhere.
Apply a thin or light coat of a water-repellent preservative sealant to the cedar siding with a paintbrush. When applying the sealant, use a back and forth motion with the paintbrush. This works the sealant into the grain of the wood. The sealant helps seal the cedar siding against moisture. Allow the sealant to dry according to manufacturer's directions before you paint the cedar siding.
Attach the paint stirring attachment to the end of your drill to mix the paint thoroughly.
Apply one to two thin coats of paint with the brush. If you are using two coats of paint, allow the first coat to dry as recommended by the manufacturer. If the weather is damp or cold, you need to adjust the drying time to a longer period.