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Yes, you can paint over old exterior paint, but success depends on the condition of the existing paint and proper surface preparation. If the previous coating is in good shape (not cracked, peeling, or flaky), you can paint over it with less prep work. However, for the most durable and professional-looking results, follow these key preparation steps:

• Clean the Surface: Thoroughly clean the exterior to remove all dirt, grime, and mildew. A pressure washer can be very effective for this.

• Scrape and Sand: If the old paint is peeling, cracked, or flaky, you must scrape off all loose paint. After scraping, sand the surface to create a smooth, even base for the new paint. Sanding is especially important for wood siding.

• Apply Primer: Using a quality exterior primer is highly recommended. It ensures the new paint adheres properly, improves durability, and provides a uniform finish. If you are painting a lighter color over a dark one, a tinted primer will help cover the old color more effectively.

Some brands offer paint-and-primer-in-one products for convenience. Taking the time to prepare the surface properly will not only increase your home's curb appeal but also help protect your siding and extend its life.

You can apply waterproofing over paint, but you won't get as much protection as you would if you painted the surface with a waterproof paint from the get-go. Not all waterproofing methods are compatible with painted surfaces, and they may not adhere well. This is especially true if the paint is glossy, old, or flaking. Waterproofing sealers are primarily meant to be applied to porous surfaces, like concrete, wood, or brick. 

With patience, you can often save a dried paintbrush. Soak the bristles overnight and clean the brush as you would any other time. You'll likely have to repeat the cleaning steps, including soaking, more than once.

You do not have to remove lead paint if the surface is not chipping or peeling or if there are no pregnant people or children under the age of six who live in or regularly visit your home. Lead paint is a particular risk for young children whose brains and bodies are not fully developed. Experts strongly recommend that you call a pro to remove lead paint if it’s peeling or flaking, no matter who lives in the home. You can experience lead poisoning by breathing in or ingesting just a small amount of it.