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There are a handful of reasons why your drywall anchors are breaking. Using the wrong type of anchor is the most common problem, so always make sure you’re using the best option for a particular project. That there are electrical wires or plumbing where you’ve placed an anchor or that your drywall is weak are two other possible causes. 

Yes, you can install drywall over plaster, but there are important factors to consider. While it can create a smooth, flat surface, it is often not the best approach. Installing drywall over plaster will increase the wall's thickness, which can cause issues with existing window and door frames that may no longer fit. You might also need to adjust power outlets to keep them accessible. A better, though more expensive, option is to remove the old plaster and lath entirely before installing new drywall. Drywalling directly over plaster seals in the old material, and if any problems arise later, you will need to remove both layers down to the structural beams for repairs. Given the potential complications, this job is best handled by professionals.

Drying alone can take 1 to 4 hours to dry to the touch per plaster layer, but some types of plaster take several hours longer to dry. However, this doesn’t mean the job is done because plaster doesn’t fully harden until it cures, which can take a few days to a couple of weeks. It may take even longer if you’re building a new, pretty thick plaster wall. Allow the plaster to cure before painting it.

When used correctly, drywall patch kits can work well. However, there are limitations. Specifically, these kits can only cover holes up to 5 inches in diameter. For anything larger than that, you’ll need to cut out the affected section of drywall and replace it with a new piece. That’s a far more complicated process that involves buying the right type of drywall, finding the wall studs, cutting into your wall, and screwing the replacement drywall in place.