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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.

There are times when you should remove all exterior paint before repainting. This includes when you need to get rid of lead-based paint (which should be done by a pro), or if you need to apply a different finish than what’s already there. Your house may also have too many pre-existing layers of old paint, in which case you’ll be better off getting rid of the old layers first.

The list of what removes caulk residue includes rubbing alcohol. In some cases, rubbing alcohol can also help remove water-based caulk. However, old caulk or caulk that’s in layers from years of upkeep and projects might prove to be too much for simple rubbing alcohol and may require a caulk-removing solution from a home improvement store.