Yes, wood planter boxes need drainage holes to allow excess water to escape, preventing root rot and waterlogged soil. Without adequate drainage, the soil can retain too much moisture, leading to unhealthy plants and potential wood rot. Place the holes evenly across the bottom and consider adding a layer of gravel or small stones for additional drainage. If the planter is lined with plastic, make sure the drainage holes are cut through the liner as well. Elevating the planter slightly will also help excess water flow out more effectively.