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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.

Using a wire brush, forcefully scrub the surface to remove paint from metal. You’ll want to remove any lingering rust, too. For larger areas with caked-on rust, you may need to use a wire brush drill attachment. If the paint still won’t budge, apply a chemical paint stripper to the area and scrape off the paint, after following the paint stripper’s instructions.

Some homeowners have luck using pressure washers, but this only works for old or weaker concrete sealants and with very powerful pressure washers. You’ll get better results by pressure washing water-based sealants. However, it’s worth trying on any sealant if you’re hoping for the least toxic, least expensive, and most DIY-friendly option. To try this method, rent or buy the most powerful pressure washer you can find and take several passes at the concrete, completely pressure washing the entire area. You may need to repeat the process multiple times to see results.