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Homeowners insurance generally won’t cover stucco damage unless it’s caused by a covered event like a storm or fire. You’ll need to pay out of pocket for damage caused by age, wear and tear, lack of maintenance, or faulty installation. Consult your policy for the specifics of what stucco damage is covered and what isn’t.

Failing to repair damaged stucco can lead to significant problems. Cracks can grow and deepen, allowing water and moisture to get behind the stucco. This moisture intrusion can cause water damage, structural issues, and mold or mildew growth. Delaying repairs will likely cost more in the long run as the damage worsens, so it's best to repair your stucco as soon as you notice any signs of damage, such as cracks, holes, or discoloration.

The best way to assess that your stucco needs repair is to inspect it, both visually and physically. If you notice cracks, chips, or staining, that’s a good indication that your stucco could use some TLC by a professional. Additionally, if you touch an area that feels soft and has a little “give,” you should consider repairing it as soon as possible to avoid further damage, both to additional stucco spots and to your home’s structure. 

A standard drill will work just fine if you’re drilling small holes, and only a few of them. But anything with a diameter larger than 3/8 inch is best done with a hammer drill, since it is stronger, faster, and also makes your drill bits last longer. While you don’t absolutely need a hammer drill for stucco, it is a worthy investment if you think you might drill more holes down the road.