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Water pooling, uneven surfaces, or basement leaks are indicators.

It depends on the model of your pool. You’ll always have to level the topsoil, but most vinyl-lined pools require an additional 1- to 2-inch layer of sand to protect the liner. This way, when a foot kicks down to the bottom of your pool, it’s not scraping the liner against the hard ground. If your pool isn’t vinyl-lined, you can skip this step or add a layer of another base material, like decomposed granite. Always check your manufacturer’s instructions before you begin.

Yard grading is a key component of proper drainage because runoff naturally moves with respect to gravity. If you have low spots in your yard, rain and snowmelt will settle there and oversaturate the soil, promoting root rot and fungal growth. If the low spots are near your home’s foundation, you could even end up with foundation leaks or structural damage due to poor yard grading.

For minor unevenness, you don't necessarily need to remove grass before leveling. You can apply a topdressing mixture to fill in low areas and even out the surface. However, for more significant unevenness or deep depressions, it might be necessary to temporarily remove the grass to ensure proper leveling and soil compaction. After filling and leveling, you can replace the grass or consider reseeding the area.