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Scrape softened caulk with a putty knife or slice hardened caulk with a utility knife. Hard-to-remove caulk generally requires more time exposed to a softening solution, like a commercial product or rubbing alcohol. A few hours to a day later, the softened caulk will come off with the help of common household tools. In many cases, you can grab needle-nosed pliers for caulk with multiple old layers and pull the material off its base. 

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 paint over cracked paint, but only if you properly sand down the damaged areas. Once the surface is as smooth as you can get it, clean the walls and let them dry before applying a new coat of paint. Painting over cracked paint without sanding or cleaning beforehand will not cover up the cracks and may even make them look worse.

You don’t necessarily have to remove all the old paint before repainting your deck, but it’s best to remove as much as possible to ensure a smooth and long-lasting finish. Prioritize scraping off loose, peeling, or flaking paint, and sand down rough areas to create a smooth surface for the new paint to bond with.